In January 2014, Bill Murray created a minor pop-culture event by participating in a Reddit Ask Me Anything chat to promote his latest movie, The Monuments Men. He isn’t a recluse—he appears in movies regularly, and he’s a favorite guest of David Letterman—but he’s probably as far off the grid as someone can be while still remaining a major movie star.

It didn’t seem to matter that Murray was promoting one of his lesser movies, or that he isn’t the star of The Monuments Men, but part of its ensemble. All that mattered was that Bill Murray was talking directly to his fans in a manner that was funny, smart, charming, and at times even mildly revealing. It was, in other words, precisely what fans wanted from him. In his own strange way, Murray has always been a man of the people, a performer whose essential relationships are with his fans and fellow artists, not with the media, studios, publicity people, or any other part of a show-business machine he’s done everything in his power to avoid. In that respect, the AMA made perfect sense.

It’s tempting to suggest that Murray has learned how to cultivate an air of mystery. But the truth is that mystery can’t be cultivated, any more than charisma or magnetism can: An artist either has it or doesn’t. Murray, remarkably, has been able to maintain it even after appearing in Larger Than Life, Osmosis Jones, and multiple motion pictures in which he provided Garfield’s voice. That helps explain the remarkable longevity of Murray’s career. Of everyone Murray started out with at Saturday Night Live, he’s the only one who has gone the distance, the one who hasn’t died, semi-retired, or been rendered irrelevant by the cruelty of time and a lack of reverence for his comic elders.

In his earliest incarnations, that sense of mystery often took the form of ironic reserve. As Murray got older, his mystery began to take on a more existential dimension. Funny people are expected to give everything of themselves, to pander for viewers’ affection and laughter, but Murray holds audiences at arm’s length. In Broken Flowers and Rushmore, he simultaneously seems to be giving all of himself and nothing, to be exposing his soul and a paralyzing inner emptiness. When that ironic distance shatters, as it does often in his more recent films, the result can be devastating.

It was similarly touching during the Reddit AMA when Murray was asked about his best memories of meeting a fan. He answered with an anecdote about a woman who was lifted from a deep depression by Caddyshack. He added: “I know I'm not saving the world, but something in what I’ve learned how to do or the stories that I’ve tried to tell, they’re some sort of representation of how life is or how life could be. And that gives some sort of optimism. And an optimistic attitude is a successful attitude.”

The Saturday Night Live And National Lampoon Years: (1975-1980)

2.5 Tarzoon: Shame Of The Jungle 1975 4.0 Next Stop, Greenwich Village 1976 3.0 Mr. Mike’s Mondo Video 1979 3.5 Meatballs 1979 0.5 B.C. Rock 1980 1.0 Where The Buffalo Roam 1980 1.0 Loose Shoes 1980 4.0 CaddyShack 1980

That optimism was necessary in 1977 when Murray stepped into what might have been the single most challenging position in show business at the time—replacing the hottest star in comedy (Chevy Chase) on Saturday Night Live, the hippest, most talked-about show on television. Murray specialized in playing show-business phonies, from his smarmy lounge-singer Nick to his role as an entertainment correspondent on “Weekend Update.” Bill Murray’s movie career emerged from the primordial stew of Saturday Night Live, the various offshoots of National Lampoon (most notably The National Lampoon Radio Hour), and Second City, and his first appearances on the big screen are offshoots of these affiliations—though his first film appearance, as Nick Kessel in 1976’s Next Stop, Greenwich Village, actually predated his turn on Saturday Night Live. Paul Mazursky’s wry, evocative coming-of-age movie about his early days as an actor doesn’t call upon Murray to do much more than look striking with a mustache, in his role as a Greenwich Village eccentric. Murray only has a few words of dialogue, but it’s telling that even at this early, embryonic stage of his career, he already played the kind of character people told stories about, the subject of legends.

Murray was among a smattering of Saturday Night Live veterans lending their voices to a raunchy but only intermittently inspired parody of Edgar Rice Burroughs’ iconic jungle denizen, Tarzoon: Shame Of The Jungle, co-directed by National Lampoon cartoonist Picha, and co-written by Saturday Night Live veterans Anne Beatts and Michael O’Donoghue. (The film was released internationally in 1975, but only made it to the States in 1979.) Murray also lent his voice to B.C. Rock, a crude animated prehistoric comedy also directed by Picha that was released internationally in 1980, and arrived Stateside in 1984. The film aspires to be a scorching social satire in the Fritz The Cat vein, but is “adult” only in the most juvenile sense, with Murray voicing an enraged dragon who shoots fire out of his anus instead of his mouth.

Murray also pops up ever so briefly as a sideways-talking bum with distinctly Carl Spackler-like vocal inflections in man-on-the-street segments in the 1979 curio Mr. Mike’s Mondo Video. The sometimes-brilliant, sometimes-insufferable pop-art provocation was created by Murray’s pal Michael O’Donoghue as a special to run on NBC during one of Saturday Night Live’s off weeks, but was released theatrically instead when NBC rejected the project on the grounds of taste, content, and all-around decency. Murray makes another brief appearance in Loose Shoes, a ramshackle, low-budget, and often screamingly unfunny sketch-comedy riff on coming attractions that feels uncannily like early Saturday Night Live, only terrible. It’s notable only for Murray’s performance as an epicurean death-row inmate desperate to avoid his imminent execution.

1979’s Meatballs was hastily thrown together. Murray’s idiosyncratic working habits are a part of his legend, so while many people would view a movie vehicle as a golden opportunity, the cast and crew of Meatballs began filming not knowing whether its star would even show up, even after he brought Harold Ramis in to punch up the screenplay to suit his gifts. Thankfully that uncertainty disappeared when Murray stepped onto the set as Tripper Harrison, the head counselor at a shabby camp at war with a snooty rival. What’s remarkable about watching the Ivan Reitman-directed Meatballs today is how wonderfully, wildly inappropriate it is for the children who have long been its target audience. It’s a camp comedy in the same way Slap Shot is a hockey comedy: It’s raunchy, randy, and keenly attuned to the raging hormones of both the kids in the cast and the teenagers in the audience.

From the beginning, Murray wins sympathy by never seeking it. During his scenes with a sensitive camper played by Chris Makepeace, Murray responds to him rather than playing to the audience. The scenes between Murray and Makepeace form the film’s emotional crux, and are crucial to the film’s success and enduring popularity. For all its laziness, Meatballs has an irresistible appeal to kids: For 100 minutes or so, Bill Murray becomes their good friend and spiritual mentor. The potency of that appeal doesn’t end with Meatballs, which wasn’t the last time he played a conflicted father figure.

Murray’s contributions to Tarzoon, B.C. Rock, Loose Shoes, and Mr. Mike’s Mondo Video were mostly a matter of showing up and doing a little shtick. The same can’t be said of Murray’s role as his hero, Hunter S. Thompson, in 1980’s Where The Buffalo Roam. Murray went full-on Method to portray Thompson, hanging out with the writer in a bid to capture his essence, mimicking his speech patterns, and throwing himself into the role with such feverish intensity that when he returned to his day job at Saturday Night Live post-filming, he was still in character as the living embodiment of gonzo journalism.

It was all for naught. Where The Buffalo Roam approaches its subject from a worshipful place; it doesn’t want to understand Hunter S. Thompson, it just wants to party with him. Buffalo’s adulation of its subject does Thompson a disservice, and the film has no idea how to make the writer’s quicksilver prose cinematic, or even coherent. The film’s framing device has Thompson slurring sideways at a typewriter while remembering his friend and sidekick Carl Lazlo (Peter Boyle), as scenes from their misadventures haltingly spill out in a collection of flashbacks that barely constitute a movie. Murray is feverishly committed to the role, and intermittent moments offer a tantalizing glimpse of the dramatic actor to come, but he’s playing a cartoon rather a human being. The film’s broad, Animal House-inspired take on the slobs-vs.-snobs comedy robs the relationship between Thompson and Lazlo of any real depth. Where The Buffalo Roam wasn’t the last vehicle to fail Murray, or to make poor use of his talents, but it could be the most heartbreaking.

Murray rebounded nicely that same year with Caddyshack, which paired him with Rodney Dangerfield, Ted Knight, and Chase. Murray’s investment in Caddyshack was minimal. He simply showed up on set for a film co-written by his brother Brian Doyle-Murray (who also appears in the film) and directed by Ramis, and improvised his entire performance as Carl Spackler, a groundskeeper at a snooty country club engaged in all-out war with a sassy gopher. In the process, he created a slacker hero for the ages, a singularly inspired cross between the perpetually thwarted Wile E. Coyote and Marlon Brando in Apocalypse Now. Murray babbled divine nonsense and emerged the MVP of an all-star comedy dream team, stealing the film from stars at the height of their powers. Caddyshack wasn’t a competition, but Murray won it all the same.

Caddyshack encapsulated all that was new and exciting about comedy in 1980, and nothing was more electrifying than a young Bill Murray working without a net and without a script. The same held true in the decades to come, albeit with some strikingly different results.

The Comedy Superstar Years: (1981-1986)

2.5 Stripes 1981 4.0 Tootsie 1982 3.5 Ghostbusters 1984 4.0 Nothing Lasts Forever 1984 3.0 The Razor’s Edge 1984 4.5 Little Shop of Horrors 1986

In 1981, Murray reunited with Ramis and Reitman for the military comedy Stripes. The film began life as a Cheech And Chong vehicle, but then Columbia hired Ramis to rewrite what everyone agreed was a pretty lousy script, turning it into a vehicle for Murray and himself. The result was a ramshackle slobs-vs.-snobs comedy whose stubborn refusal to say anything remotely satirical or irreverent about the military or American foreign policy at the height of the Cold War almost qualifies as impressive. Otherwise, Stripes is a remarkably toothless piece of filmmaking, poorly directed and sloppily written. But it was an enormous box-office hit all the same, and thanks largely to Murray’s enormous charisma and popularity, it’s attained the status of a pop classic without being particularly good.

When 1982’s Tootsie came out, Murray’s uncredited participation must have seemed perplexing. What was one of the hottest comedy stars in the planet doing working as part of an ensemble? Murray’s involvement makes a lot more sense today, when Tootsie can be looked at as a successful test run for Murray’s career-revitalizing reinvention as a dramatic character actor. With Tootsie, Murray embraced being part of a film’s sprawling tapestry rather than the engine that drives it. Sydney Pollack’s blockbuster unexpectedly but smartly cast Murray as the playwright roommate of the struggling actor played by Dustin Hoffman, and in a wonderful performance characterized by deadpan under-reaction, he remains matter-of-fact about his friend’s strange detour into professional cross-dressing.

Murray stepped in to play wisecracking parapsychologist Dr. Peter Venkman in 1984’s Ghostbusters, a role originally written for John Belushi by his friend, partner, and fellow Saturday Night Live alum Dan Aykroyd. Murray’s Venkman is a parapsychologist who doesn’t seem too invested in the business of parapsychology, viewing it as an elaborate hustle to score money and women. He’s so cynical that he doesn’t even believe what he sees with his own eyes, responding to demon dogs and marshmallow monsters as if the only logical response to a crisis is a withering zinger. Murray carries the film, yet remains separate from the action, a wry outsider delivering a sarcastic running commentary on a New York that has devolved from an everyday hellhole into a gothic supernatural hellhole, with only himself and his fellow Ghostbusters to save the day.

The respect Murray has commanded throughout his career didn’t render him immune to the suspicion that inevitably greets prominent funny men intent on making serious artistic statements as dramatic actors. Accordingly, The Razor’s Edge, Murray’s 1984 debut as a dramatic leading man, was greeted by scathing reviews and atrocious box-office. An adaptation of an M. Somerset Maugham novel about man’s search for meaning in an often cruel, random universe, the film casts Murray as a globe-trotting spiritual searcher of the Jazz Age. The young comic performer hadn’t yet acquired the world-weariness and bone-deep sadness that characterize his later dramatic performances, so his disillusionment sometimes registers as blankness rather than pathos. Murray looks distinctly out of place, an unmistakably 1980s goofball hurtled back into a resurrected past. He eventually grew into these kinds of roles, but in 1984, they still fit him like an older sibling’s outsized clothing.

The Razor’s Edge is an icy, remote movie enlivened by hot flashes of raw, searing emotion, like a eulogy Murray’s Larry delivers for his hard-drinking, hard-living, hard-ass mentor Piedmont (played by Murray’s older brother, Brian Doyle, in his greatest dramatic performance). The eulogy was inspired by Murray’s own feelings toward Belushi, whom he phantom-eulogizes as a repugnant man of regrettable personal hygiene who was “despicable” and “enjoyed disgusting people.” When Murray, as Larry, closes his eulogy of Belushi-by-way-of-Piedmont by tearfully asserting, “He will not be missed,” his sarcasm becomes poignant and beautiful, a devastatingly effective rhetorical tool. Comedy, when practiced as hard as Murray and Belushi practiced it in the 1970s, was a form of warfare, with casualties all its own.

Remarkably, the same year Murray and Aykroyd helped make Ghostbusters, one of the top-grossing and most beloved comedies of all time, they co-starred in an even more charming and inspired fantasy comedy that has never been officially released in any form (though it can currently be found in its entirety on YouTube). Nothing Lasts Forever is a unique fantasia produced by Lorne Michaels and written and directed by in-house Saturday Night Live filmmaker Tom Schiller in the style of half-forgotten studio efforts from the 1930s and 1940s. The film nails the look and feel of misremembered trifles from the early sound days, but with its own electric spirit. Shot in black and white with occasional forays into Technicolor, Nothing Lasts Forever has a plot that could easily double as a waking dream. Gremlins’ Zach Galligan stars as an ambitious young artist who ends up working for the Port Authority of New York after he fails a test to become an artist. At that point, he discovers that an underground society of hobos secretly rules the world, and he heads to the moon on a bus populated by senior citizens, special attraction Eddie Fisher (playing himself), and a sky host played by Murray, whose tight-lipped smarminess hides sinister motives. Just as Nothing Lasts Forever feels like a 79-minute version of one of the quirky confections Schiller made for Saturday Night Live, Murray’s performance feels like an extension of his SNL character work.

Ghostbusters made Murray one of the hottest stars around, but rather than exploiting his professional momentum and making a fortune in the process, he took a step back. 1985 passed without a single screen appearance from Murray, and in 1986, he only made a brief but attention-grabbing appearance in Frank Oz’s delightful adaptation of the hit musical Little Shop Of Horrors, as a patient so masochistic, he flummoxes Steve Martin’s sadistic dentist by taking the fun out of torture.

Years Of Transition (1988-1993)

3.0 Scrooged 1988 2.0 Ghostbusters II 1989 3.5 Quick Change 1990 3.5 What About Bob? 1991 3.5 Mad Dog And Glory 1993 4.5 Groundhog Day 1994

Murray returned to ghostly realms with the 1988 Christmas hit Scrooged, which began life as a pitch-black Christmas Carol spoof written by Michael O’Donoghue, the original Saturday Night Live’s revered Prince Of Darkness, and O’Donoghue’s writing partner Mitch Glazer. Ghostbusters’ astonishing success should have given Murray the leverage to protect O’Donoghue and Glazer’s script, which turned Scrooge into a black-hearted TV executive named Frank Cross, which let O’Donoghue take aim at his favorite target—the greed and venality of the television industry—in the kind of big movie that gets played on television every year.

Alas, Paramount was understandably more interested in reproducing Ghostbusters’ box-office than in serving a cult humorist’s warped, wicked satirical vision. So O’Donoghue and Glazer’s script got watered down by director Richard Donner (who also produced), whose background was rooted in action films like Superman and The Goonies, not cutting-edge satire. Scrooged is consequently a compromised movie that has the strange quirk of being alternately too mean and too nice. Yet when Cross, now a changed man, breaks into a live production of A Christmas Carol to deliver an impassioned monologue about the true meaning of Christmas, it’s unexpectedly moving to see this chilliest of customers break down, lose his cool, and give himself over to the Christmas spirit. It’s a moment made effective by the notes of genuine terror and confusion Murray brings to the scene.

Ghostbusters II represents another unfortunate missed opportunity. The film was ushered into existence by the demands of commerce, but Dan Aykroyd and Harold Ramis’ screenplay nonetheless overflows with clever ideas. Unfortunately, they’re killed by the indifferent execution. The film opens with the Ghostbusters in a state of disgrace, and Venkman reduced to leveraging his waning fame to host a bogus paranormal talk show, until a massive influx of bad vibes hits New York, creating a new and terrifying supernatural crisis. The idea of Venkman as a second-rate television personality is an inspired one that appeals to Murray’s genius for playing phonies, but the film fails to inject its clever notions with actual jokes. There’s wit at the film’s fringes, but a hollowness at the core. Ghostbusters II leaves most of the heavy lifting—and ghostbusting—to Venkman’s colleagues so Murray can play romantic leading man to Sigourney Weaver and do shtick with her baby, but his performance feels as arbitrary as the film itself.

When original director Jonathan Demme dropped out, Murray stepped in to make his directorial debut (alongside co-director Howard Franklin) with 1990’s Quick Change, an adaptation of a comic novel by Jay Cronley that had already been adapted into the French-Canadian comedy Hold-Up. Murray plays Grimm, a man fed up with the frustrations of big-city life who robs a bank while dressed a clown, then confronts a city so rife with lawlessness that it makes him and his criminal accomplices (Geena Davis and Randy Quaid) look like amateurs by comparison.

Murray smartly casts himself as the film’s straight man, which is no mean feat, since he spends much of the film in clown makeup. Working from Franklin’s smart, elegantly constructed script, Quick Change builds into a symphony of mounting frustration as three people who just want to get out of New York are perpetually thwarted by forces that make robbing a bank easier than getting to the airport on time. There’s a strange continuity between Ghostbusters II and Quick Change, both of which pit Murray and his helpers against the ill will of the people of New York. But Quick Change is defined by an old-school sense of comic craftsmanship, and Murray confidently carries the film while letting the supporting cast get most of the laughs, particularly Quaid, who is hilarious and poignant as one of his signature simpering man-children. Unfortunately, the comedy underperformed commercially, and remains Murray’s only directorial credit to date.

Murray delivers such a sunny, upbeat performance as a professional neurotic in 1991’s What About Bob? that it’s easy to overlook the film’s bracing darkness. Murray’s Bob is a whirling dervish of runaway anxiety who gloms onto the family of narcissistic psychiatrist Dr. Leo Marvin (Richard Dreyfuss), who seems to see his patients, and all humanity, as annoyances to be endured for the sake of attaining celebrity and wealth. Marvin wants nothing more than to be left alone, and is apoplectic when Bob, a new client, shows up unexpectedly at his beach home, then obliviously insinuates himself into Marvin’s longsuffering family.

Murray accomplishes the tricky tonal feat of being lovable enough to make the family’s preference for him over their efficient but joyless patriarch palatable, yet annoying enough to make the doctor’s rage toward him understandable. Directed by Frank Oz, the film is defined by a stubborn refusal to force emotional growth on its leads. Murray’s raw nerve of a shambling man-child never grows up, and Dreyfuss’ irritable intellectual never loosens up, or accepts that he cannot control everything. Murray conveys an uncharacteristic emotional neediness that nicely offsets the film’s cynicism and complements Dreyfuss’ prissily controlled performance. Murray has seldom played a character sweeter or more prone to engender homicidal rage.

At the time of Mad Dog And Glory’s 1993 release, the film was touted as a radical change of pace for Murray, who was leaving straight-up comedy behind to play a dramatic role in a gritty character study opposite no less an icon than Robert De Niro, for director John McNaughton of Henry, Portrait Of A Serial Killer fame. In retrospect, the film feels more like an organic evolution than a dramatic leap. On Saturday Night Live, Murray specialized in playing terrible entertainers whose awfulness implicates show business as a whole. Here, Murray makes the most out of a tragicomic subplot involving a gangster’s doomed attempts to reinvent himself as a stand-up comedian whose mob-centric material flops with anyone not already on his payroll. Murray plays Frank Milo as both terrifying and pathetic, a pathological narcissist intent on improving himself through psychoanalysis and spiritual growth, but without realizing he’s rotten to the core. Frank is one of a series of spiritual searchers in the Murray filmography who come to the terrifying realization that the money and power they’ve accrued mean nothing, and redemption lies not in controlling other people, but in making genuine human connections. Frank’s tragedy is that he’s genuinely incapable of moral and spiritual growth, no matter how desperately he tries.

That isn’t true of Phil Connors, the character Murray plays in the same year’s Groundhog Day. The final, greatest collaboration between Murray and director/co-writer Ramis Trojan-horses a quietly profound exploration of what it means to be human inside a perfectly crafted mainstream comedy. Connors is a narcissistic Pittsburgh weatherman who, like Frank, sees other human beings as stepping stones toward what he wants. The film follows him, along with cameraman Larry (Chris Elliott) and producer Rita (Andie MacDowell), on a trip to Punxsutawney to find out whether the weather-predicting groundhog Punxsutawney Phil will see his shadow on Groundhog Day. The assignment feels like an eternity in folksy purgatory even before a strange quirk in the universe results in Phil, and only Phil, waking up to the exact same day every single morning.

In the film’s early going, Murray gives his grouchy misanthrope some of the dyspeptic, grouchy grace of W.C. Fields. He’s a bastard, but he’s our bastard, and Murray is in his element playing yet another show-business phony whose plastic smile and facile charm masks a heart overflowing with bitterness and pointless, self-defeating ambition. Over the course of the film, Phil learns how to be a good man by letting go of his need to control and manipulate situations. He learns to live for other people, to value their happiness over his own. In the process, he redeems himself and genuinely, honestly wins the heart of the woman he loves.

Groundhog Day is written and directed with almost mathematical precision. It methodically charts its protagonist’s spiritual evolution as he attempts to think his way out of a dilemma that’s unique to him, yet comments adroitly on the mysteries of life. Murray’s performance essentially encapsulates his entire career, past and future. His performance evolves slowly but surely from the smarmy glibness of the parts he played on Saturday Night Live to the depth, richness, and ineffable sadness of the dramatic roles that followed. It’s a film that says a lot about humanity as a whole, but also much about Murray in particular.

Character Roles And A Brief Period In The Wilderness (1994-1998)

4.5 Ed Wood 1994 3.0 Kingpin 1995 1.0 Space Jam 1996 2.0 Larger Than Life 1996 2.5 The Man Who Knew Too Little 1997

Groundhog Day casts such a long shadow that it dwarfed another fine Murray performance as Bunny Breckinridge, Ed Wood’s friend and collaborator in 1994’s Ed Wood. It’s a small role overshadowed on one side by the goofy bigness of Jeffrey Jones as bogus psychic Criswell, and by the tragicomic sadness of Martin Landau’s Bela Lugosi on the other. Still, Murray manages to make an indelible impression in a cast filled with showstoppers and scene-stealers. He makes an understated turn as a man who manages to hold on to some of his perpetually embattled dignity, despite professionally occupying a spot somewhere underneath the sewer. It’s not a goofy comic solo like Little Shop Of Horrors; it’s a performance by a real actor that foreshadows a lot of the stellar character work Murray went on to do.

In 1996, Murray returned to playing the kind of smarmy, narcissistic bastards he specialized in on Saturday Night Live with his scene-stealing turn as legendary bowler Ernie “Big Ern” McCracken in Kingpin, the Farrelly brothers’ follow-up to Dumb & Dumber. Murray plays the legend of the lane as a showboating phony with an endless array of toupees and gaudy outfits, each more horrifying than the last, a pathetic peacock lost in a bubble of unjustified self-love. A good portion of the Farrellys’ montage-heavy sports comedy is devoted to Murray’s post-strike vamping, and the film benefits from having an actor who doesn’t need good lines, or any dialogue at all, to be funny.

That same year, Murray lent his presence to a different kind of sports comedy in Space Jam, playing a family-friendly version of himself opposite the vast, comedy-killing black hole that is Michael Jordan. At least the Chicago sports buff got to hang out with Michael Jordan for a while, so he has that going for him, which is nice. Also in 1996, Murray re-teamed yet again with Howard Franklin for Larger Than Life, a family-friendly comedy featuring Murray as an inept motivational speaker who receives an elephant as an inheritance and must travel to Los Angeles to deliver it to an animal trainer. In the featherweight comedy, a lost, defeated Murray is reduced to playing sidekick to an outsized pachyderm. In the film’s only memorable sequence, a speed-crazed trucker played by a young Matthew McConaughey, who after Larger Than Life was able to cross “steal a movie from Bill Murray” off his bucket list.

Even at the time of its release, 1997’s The Man Who Knew Too Little felt like a throwback, both for Murray and for comedy as a whole. By that point, studios had all but stopped making goofy, family-friendly PG comedies about well-meaning klutzes who wind up embroiled in international intrigue. Murray nevertheless commits himself to the well-meaning idiocy of Wallace Ritchie, a good-natured doofus who works at a Blockbuster in Des Moines, and stumbles into international espionage when he mistakes a genuine spy situation for the interactive live-acton spy game his brother signed him up for as a birthday present. Murray mugs his way through the film with an idiot grin of stupefied satisfaction as Wallace bungles from one life-threatening situation to another, oblivious to the real danger he’s in. It’s a fun, goofy physical performance in a trifle unworthy of Murray’s talents. Murray was simply too smart and talented to go on playing the fool deep into middle age. Soon, he wouldn’t have to.

Reinvention (1998-2001)

4.5 Rushmore 1998 2.0 Wild Things 1998 2.5 Cradle Will Rock 1999 3.0 Hamlet 2000 2.0 Charlie’s Angels 2000 4.5 The Royal Tenenbaums 2001 2.0 Speaking Of Sex 2001 2.0 Osmosis Jones 2001

Rushmore changed the course of Murray’s career so dramatically that it serves as a useful dividing line in his filmography. Wes Anderson’s breakthrough film cast Murray as Herman Blume, a millionaire businessman cursed with ineffable sadness. He’s amassed millions and created a family without ever losing his adolescent alienation, leading a life with no joy in it until he stumbles upon Max Fischer (Jason Schwartzman), the poorest student at Rushmore. Max overflows with such bravado and self-confidence that early in their relationship, Herman asks him what his secret is, since he seems to have it all figured out. The truth is that Max is every bit as broken and lost and confused as Herman; he just isn’t ready to admit that to himself, let alone to the world, so he hides behind extracurricular activities and epic quests, most notably to win the heart of melancholy teacher Rosemary Cross (Olivia Williams), a doomed mission that puts him in direct conflict with Herman.

Fischer and Blume emerge as strangely simpatico figures: a boy with nothing in the world but energy and hope, and a man with everything but those qualities. Rushmore ingeniously pairs a boy in a furious hurry to grow up and a man all too cognizant of the compromises and sadness of adulthood, one who wants more than anything to discover a portal to the innocence and optimism he presumably once felt. In Murray, Anderson found an actor singularly equipped to play a man with the body of a broken-down middle-aged alcoholic, and the impish spirit of an eternal child.

Rushmore didn’t change Murray’s image so much as it deepened and enriched it. The hint of melancholy that long shaded Murray’s performances evolved into an exquisite misery, reflected in the oceans-deep pain in Herman’s eyes when, late in the film, he answers a question about how he’s doing now that his wife has divorced him with the heartbreaking understatement, “I’m a little bit lonely these days.”

From the sublime to the ridiculous: John McNaughton’s 1998 erotic thriller Wild Things is a lurid, hyperventilating softcore romp and cult classic remembered primarily for an oft-rewound threesome involving stars Matt Dillon, Neve Campbell, and Denise Richards. In a film that doesn’t distinguish between intentional and unintentional laughter, Murray delivers an inspired comic performance as Kenneth Bowden, a sleazy lawyer fond of powder-blue suits and medically unnecessary neck braces who represents Dillon’s Sam Lombardo, a one-time Florida “Educator Of The Year” with an unfortunate predilection for sleeping with his students.

For better and for worse (mostly for worse), Murray has gravitated toward passion projects, often those written and directed by his fellow actors. Those include Tim Robbins’ 1999 ensemble film Cradle Will Rock, a wonderfully misguided attempt to transform a rabble-rousing tribute to the WPA’s populist spirit into a typically upbeat, mindlessly commercial Touchstone comedy. The film is a bloated mess that treats leftist social history with Pollyanna-like chipperness, but Murray is heartbreaking and hilarious as Tommy Crickshaw, a down-on-his-luck ventriloquist reduced to teaching his curious craft to a pair of incompetent, opportunistic upstarts played by Tenacious D’s Jack Black and Kyle Gass. The following year, Murray was one of the gallery of familiar faces in Michael Almereyda’s ballsy modern-day adaptation of Hamlet, starring Ethan Hawke as a grunged-out slacker Hamlet. Murray turns Polonious into one of his signature pompous phonies, an avuncular figure who doles out some of the most famous advice in literature, and adopts the pose of the benevolent mentor as a cover for his own greed and calculation.

Following Murray’s creative revival with Rushmore, his career grew increasingly schizophrenic, alternating passion projects done for no money with passionless projects done solely for money. 2000’s Charlie’s Angels, a wildly excessive adaptation of the campy 1970s jiggle-fest, directed by music-video veteran McG, falls into the second category. Murray flounders in the role of Bosley, the hapless go-between working with a trio of sexy female agents and their mysterious, never-seen overlord. Stuck in a series of campy getups and silly hairdos, Murray is palpably uncomfortable. (Murray opted out of the obligatory sequel after publicly feuding with Lucy Liu.)

Murray reunited with Wes Anderson for 2001’s The Royal Tenenbaums, this time as Raleigh St. Clair, a bearded, Oliver Sacks-like neurologist married to Gwyneth Paltrow’s Margot Tenenbaum, the melancholy object of desire for many of the characters in the film. It’s a small but pivotal role that Murray invests with a sense of romantic longing and confusion once Raleigh comes to realize that the woman he thinks he knows is fundamentally unknowable. Murray was essential to Rushmore, but here, he lets himself be just another muted color (think an autumnal grey or a faded blue) in Anderson’s cinematic palette.

In 2001, Murray reconnected with McNaughton for a third collaboration, this time playing yet another sleazy lawyer in Speaking Of Sex, an ill-fated romp about the complicated legal wrangling that ensues when a neurotic psychiatrist (James Spader) sleeps with with a sexually frustrated married woman (Melora Walters). It’s a pleasure watching old pros Murray and Catherine O’Hara play off each other as rival attorneys who find love in each other’s arms, and Murray is a hoot as a toupee-wearing, cigar-chomping sleazebag. But otherwise, this is the kind of randy, vulgar nonsense that resorts to Benny Hill-style sped-up film to goose the flailing slapstick shenanigans.

In 2001 Murray also made Osmosis Jones, a misbegotten live-action/animated comedy that reunited him with the Farrellys and put him back in the kind of goofy-dad role his Ghostbusters co-star Aykroyd specialized in, before he more or less dropped out of the business to peddle vodka and conspiracy theories. Murray plays Frank, a zookeeper whose body doubles as an animated metropolis devoted to keeping this shambling mess of a human being alive and just barely functioning by any means necessary. It isn’t a terrible idea for a film, but the filmmakers lazily steer the material into the tired world of the mismatched buddy-cop comedy. This underwritten role in a bland film wouldn’t be a highlight even if Murray’s big scene didn’t involve his character energetically vomiting on a teacher played by Molly Shannon. Is it any wonder Murray was increasingly drawn to the artsier, less vomit-intensive corners of film?

Broken Men And Cartoon Kitties (2003-2007)

4.5 Lost In Translation 2001 3.0 Coffee & Cigarettes 2003 1.0 Garfield: The Movie 2004 4.0 The Life Aquatic With Steve Zissou 2005 3.5 Broken Flowers 2005 2.0 Garfield: A Tail Of Two Kitties 2006

Sofia Coppola’s Lost In Translation’s casts Murray as Bob Harris, a fading American movie star who travels to a posh hotel in Tokyo to make $2 million shooting a whiskey commercial. The minions of the ad agency that hired him shout commands that are, per the title, never translated, adding to the film’s sense of cultural dissociation. Murray lets the lapses in Bob’s façade of strained politeness tell the story of a man who’d fallen out of step with the world even before he entered a foreign metropolis where he towers over everyone, where he feels like no one understands him because they literally don’t. On the run from a life seemingly dominated by interior-decorating requests from his nagging, never-seen wife, Bob finds a spiritual kinship with Charlotte (Scarlett Johansson), a similarly adrift American at the hotel with her scatterbrained photographer husband (Giovanni Ribisi). Charlotte and Bob bond over dizzy nights spent drinking sake and singing karaoke, and over their mutual sense of isolation in a Tokyo that shimmers like a jewel box.

Coppola’s distressingly broad conception of contemporary Japanese culture sometimes threatens to transform Bob into a straight man in a city full of crazies. Lost In Translation can be mean and cheap around the edges; it makes its protagonists’ melancholy stand out even more sharply by surrounding them with caricatures. But Murray and Johansson’s chemistry lends the film soul, and its romance is all the more powerful for never being consummated. Lost In Translation famously ends on a wonderfully enigmatic note, with Bob whispering something unintelligible into Charlotte’s ear that seems to give her a sense of peace and optimism (not unlike the kind Murray talked about in the Reddit AMA when asked about his most memorable fan experience). An electric sexual and romantic charge courses through Bob and Charlotte’s relationship, but even Charlotte seems to see him as a father figure and spiritual mentor more than a love interest. That’s part of the appeal of Bob Harris: He saves Charlotte from the ennui and alienation she’s feeling, but only because, consciously or unconsciously, he knows he needs to be saved himself. The ending also taps into something essential to Murray’s appeal: the sense he has some special wisdom to impart, if only we’re lucky enough to have him whisper in our ear.

Given Murray’s penchant for working with revered auteurs, there’s some small reason to believe his claim in the Reddit AMA that he agreed to take on the role of lasagna-loving, Monday-despising fat cat Garfield out of a mistaken conviction that it was written by Joel Coen of Coen brothers fame, and not Joel Cohen of Garfield: The Movie fame. Whatever the reason, Murray’s voice and old-school king-of-the-slobs persona take center stage in the 2004 hit. There isn’t much to Garfield: The Movie, plot-wise or otherwise, so Murray desperately tries to inject life into the lethargic proceedings with a voiceover performance straining with manufactured ’tude. Murray had every reason to phone it in, to deliver a performance as lazy as the character he’s desperately trying to breathe life into. Instead, he delivered an intensely committed performance that somehow just makes everything worse. It’s a measure of how badly Murray’s performance misfires that 2006’s Garfield: A Tale Of Two Kitties represents a distinct step up in quality from its predecessor, because its Prince And The Pauper premise focuses substantially less on Garfield and more on new, less terrible characters like Tim Curry’s Prince.

Murray’s weakness for the passion projects of his fellow actors helps explain his appearance as a jester-like man of mystery with no name in Andy Garcia’s bloated, ponderous 2005 historical drama The Lost City. An alcoholic beverage forever in his hand, Murray’s character, credited only as “The Writer,” speaks in riddles and circles, in a performance that’s equal parts gratingly precious and pretentious.

But elsewhere between Garfields, Murray delivered two of his finest, most demanding dramatic performances in movies that again cast him as sad, broken men looking for meaning and connection. The first, Wes Anderson’s The Life Aquatic With Steve Zissou, takes place in the long shadow cast by the violent death of Esteban, the best friend and most important collaborator of the titular protagonist, a depressed superstar oceanographer inspired by Jacques Cousteau. Murray’s Zissou was once a beloved international celebrity whose underwater derring-do and old-school heroism inspired generations of children all over the world, including earnest young pilot Ned Plimpton (Owen Wilson), who might be Zissou’s long-lost son, but probably isn’t. As the film opens, Zissou and the crew he rules like a benevolent cult leader have fallen upon hard times and are scrambling to raise money for their next documentary, a revenge picture of sorts, in which Zissou will hunt down and kill the magnificent jaguar shark that killed Esteban.

Anderson’s flair for production design is on full and often magnificent display here, most notably in a ship that resembles the world’s largest, most elegant children’s playset. Though the relentless stylization can be emotionally distancing, Murray’s performance never lets viewers forget the sadness at the film’s core. The pain in Murray’s eyes and the quiet rage in his voice serve as constant reminders that this sometimes silly, sometimes self-defeating, always narcissistic man is motivated by almost unbearable grief. The Life Aquatic can be glib and jokey, an action-adventure whose action sequences are all delivered with sly, winking irony. Yet it finds a beating heart in Zissou’s grief and his attempts to bond with Ned, a surrogate for all the kids he inspired from afar, but who could never get close enough to their idol to see what a broken but strangely magnificent man he is. Murray attains the state of noble rot that characterizes many of his late-period performances.

It certainly characterizes the sad existential state of Don Johnston, Murray’s character in Jim Jarmusch’s 2005 film Broken Flowers. (It’s Murray’s second collaboration with Jarmusch, after his contribution to 2003’s omnibus collection Coffee & Cigarettes, which memorably cast Murray as himself, serving coffee to an overjoyed but bewildered RZA and GZA, who can’t quite believe that “Bill ‘Ghostbustin-Ass Groundhog Day’ Murray” is working as a waiter.) Like The Life Aquatic, Broken Flowers also turns on a complicated issue of parentage, as Murray’s man-child, who has eschewed the responsibilities of adulthood deep into middle age, wrestles with a fatherhood he never chose.

Broken Flowers casts Murray as a solitary computer mogul whose gorgeous yet empty home stands in stark contrast to the riotous utopia of domesticity characterized by his friend and next-door neighbor Winston (the always wonderful Jeffrey Wright) and his Ethiopian family. Don’s life of sorrowful inertia is shaken up when his latest beautiful, disappointed girlfriend (Julie Delpy) storms out. Then he receives an anonymous letter alerting him to the existence of an adult son he’s never known, but the letter omits the son’s name and all other identifying details. With Winston’s help, the aging Casanova sets out on a road trip to uncover his son’s identity, a quest that sends him spiraling through his back pages as he revisits various loves of his life, from a NASCAR widow (Sharon Stone) to a spacey “animal communicator” (Jessica Lange) to a hippie turned Stepford Wife (Frances Conroy).

When Murray first played a dramatic role in The Razor’s Edge, he clung to his comic mannerisms and tics. Murray still charms women and small children and waxes sarcastic at various intervals throughout Broken Flowers, but by this point, he had long since transcended the need for such crutches, delivering a powerfully spare performance. Murray has refined his movements and gestures such that he doesn’t seem to be moving or gesturing at all; in Broken Flowers’ shattering final moments, he attains an existential ideal of existing onscreen rather than acting, of being rather than performing. The Murray of Lost In Translation, The Life Aquatic With Steve Zissou, and Broken Flowers has transcended the irrepressible showiness of youth, the need to impress and leave a dent in the universe. In these late-period performances, Murray is like a musician who’s refined his style by eliminating all the unnecessary notes and self-indulgent vamping.

Repertory Player And Cameo King (2007-present)

3.5 The Darjeeling Limited 2007 2.5 Get Smart 2008 3.0 City of Ember 2008 3.5 Zombieland 2009 3.0 Get Low 2009 3.0 The Limits Of Control 2009 4.5 The Fantastic Mr. Fox 2009 1.0 Passion Play 2010 2.5 Hyde Park On Hudson 2012 0.0 A Glimpse Inside The Mind of Charles Swann III 2012 4.0 Moonrise Kingdom 2012 2.5 Monuments Men 2014

In real life, Murray tends to pop up in unexpected places. The Internet is littered with stories about magical nights when Bill Murray showed up out of nowhere and served tequila shots to wowed fans until 4 in the morning. That reputation lends an additional charge to Murray’s appearance as himself in 2009’s Zombieland, which casts him as the legend who shelters the protagonists after a zombie plague renders the world all but uninhabitable. Zombie-kicking badass Tallahassee (Woody Harrelson) gets to live out many people’s fantasies by smoking pot and playing Ghostbusters with Murray as they plot their next move.

A spiritual journey to the East sounds custom-made for Murray, who first visited that territory in 1984’s The Razor’s Edge, but he merely pops in for a cameo in Wes Anderson’s slight but charming The Darjeeling Limited as a harried man who misses a train caught by Adrien Brody ’s protagonist. To Murray, roles in Wes Anderson movies must feel like gifts sincerely delivered and graciously accepted, even when the role is as minor as that of Clive Badger, a lawyer who advises the dashing titular hero of 2009’s utterly delightful Fantastic Mr. Fox. Murray is once again playing a lawyer, albeit this time of the animated and animal variety, one who tends to express outrage at his clients’ actions and exhibit unexpected skills with explosives.

Murray also popped up for a blink-and-you’ll-miss-it cameo in the inessential 2008 reboot of Get Smart. The movie trades in the sly spoofery of Buck Henry and Mel Brooks’ beloved television show for generic action-comedy, but Murray gives the film a little old-school vaudevillian kick in his cameo as Agent 13, a hapless operative reduced to standing watch inside a tree. It’s telling that even when Murray turns in a cameo in a big, mainstream blockbuster, his character and performance are still defined by loneliness and isolation. That same year, Murray delivered a more lengthy and memorable performance as the unethical mayor of a dystopian underground city in the grim children’s film City Of Ember.

In his king-of-the slobs phase, Murray played men who lived with no consideration for the future. He aged into playing characters so acutely aware of their mortality that casting him as a funeral director in 2009’s Get Low almost counts as a sly joke. The film is primarily a showcase for Robert Duvall, who delivers an appropriately larger-than-life performance as Felix Bush, a small-town eccentric whose neighbors regard him as a legend on par with Paul Bunyan. He’s a heavily bearded tornado of a man who makes a rare visit into town to make arrangements for a “Funeral Party” that will let everyone in town come up and tell a story about Felix, along with a raffle whose grand prize is Felix’s property. After a more respectable funeral-home director turns him down, Felix travels to the failing business of Murray’s Frank Quinn, a nattily attired, neatly mustachioed businessman who takes the strange gig partially out of desperation, and partially as a challenge. Like so many of the characters Murray has played throughout the years, Felix is a bit of a sleaze and a charlatan, but he doesn’t entirely lack honor, and Murray gives him real warmth.

One of the strange quirks of Murray’s late-period career is that he often looks glaringly out of place, no matter where he is or who he’s playing. This is particularly true of his role as “The American” in Jim Jarmusch’s moody, hypnotic, sometimes unbearably pretentious road movie The Limits Of Control. Isaach De Bankolé stars as a stoic assassin, credited only as “The Lone Man.” Throughout the film, The Lone Man travels through Spain soaking in philosophical tirades from a series of big-name guest stars (Tilda Swinton, John Hurt, Gael García Bernal) before climactically meeting his prey, a powerful businessman played by Murray. Death is coming for many of the characters Murray has played late in his career, but seldom as directly as it is here. Murray’s justifiably terrified titan of industry, who whines about cultural corruption in the face of certain death, is perhaps the ultimate manifestation of a character he played in the later years of his career: a man whose wealth, power, and position fail to protect him from the cruelty and randomness of life.

2012’s Moonrise Kingdom reunited Murray with Anderson, who cast him as Walt Bishop, a lawyer whose orderly world is turned upside down by the disappearance of his melancholy young daughter and his wife’s affair with a local police officer. Though Moonrise Kingdom involves camping and Bill Murray, Walt isn’t the idealized older brother/mentor figure of Meatballs. He’s a grown-up who’s just as lost, confused, and in need of guidance as a daughter whose pain he feels deeply, but can’t understand. As with Fantastic Mr. Fox, the film’s extreme stylization can be emotionally distancing, but in its third act, Moonrise Kingdom attains a striking power as its various threads come together and its delicately constructed eggshell world threatens to crack. Moonrise Kingdom confirms Murray as a minimalist of rare talent, a man gifted in getting the most out of every syllable.

Murray has long played characters with complicated, emotionally fraught relationships to fame, power, and celebrity. Murray’s performance as Franklin Delano Roosevelt in the precious 2012 historical drama Hyde Park On Hudson has him treating all those elements as a lark, which is part of what makes it so anomalous in his career. Murray gives a performance of tremendous surface charm, playing the president as a hard-drinking, womanizing, twinkly-eyed father figure to a nation, but also to the many women in his own personal harem. It’s a depressingly superficial look at a complex man that gives into the kind of hero-worship and sentimentality Murray and his films have long eschewed.

Murray’s more recent film choices have been dictated by relationships and friendships more than commercial calculation. This has helped reinvigorate his career, but it also explains his presence in bizarre vanity projects like 2010’s Passion Play and 2012’s A Glimpse Inside The Mind Of Charles Swann III. Passion Play was a longstanding passion project of Murray’s friend and Scrooged co-writer Mitch Glazer, about a world-weary jazzman who engages in a trippy romance with a circus performer with angel wings. The results somehow play out even more pretentiously than that description suggests, and Murray, who stepped in at the last minute when another actor opted out, is given nothing to work with as a powerful gangster named Happy. When the only laughs in a movie with Bill Murray are of the unintentional, derisive variety, something has gone terribly awry.

Just about everything went terribly awry with A Glimpse Inside The Mind Of Charles Swann III, directed by Roman Coppola, the brother of Lost In Translation director Sofia and the sometimes-writing partner of Murray’s pal Wes Anderson. The insufferable quirk-fest reduces Murray to a sidekick of the sentient smirk that is comeback-hungry star Charlie Sheen, just another flesh-and-blood paper doll to be outfitted in outrageous costumes and plunked inside the elaborate dollhouse sets that are the film’s flimsy reason for being.

In 2014, Murray teamed up with his Fantastic Mr. Fox co-star George Clooney for The Monuments Men, another yarn about a charismatic leader who assembles a madcap group of unlikely heroes for a daring mission. The film casts Murray as a gentle Chicago architect and art collector who, in his big scene, weeps openly in the shower while a phonograph from home plays his granddaughters singing a Christmas song. It’s a moment of unabashed sentimentality that’s rare for Murray, one in which any hint of reserve or distance breaks down and he’s just a granddad weeping because he’s many thousands of miles from where he wants and needs to be.

In this moment, the prince of irony, the sultan of righteous sarcasm and retired king of the slobs is just a big old softie blubbering because he can’t be home for Christmas. It would be unfortunate if lumbering, underwhelming prestige pictures were Murray’s future, but there’s something strangely noble about seeing an icon of hipness like Murray play a moment in such a defiantly uncool way. Murray contains multitudes, and at least one of those multitudes is a sad old man. It’s also further evidence that time has not diminished Murray, it’s only enriched him.