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.