1. Nirvana, In Utero (1993)

“Teenage angst has paid off well / Now I’m bored and old” go the blunt first lines of “Serve The Servants,” the opening track on In Utero, Nirvana’s prickly follow-up to its millions-selling major-label phenomenon Nevermind. Fed up with the trappings of fame and the other baggage that went along with his success, Kurt Cobain pushed back with an abrasive album that pointedly rejected the slick, multi-layered studio sound that made Nevermind such a singles factory. The band threw down the gauntlet by hiring Steve Albini to apply his stripped-down, minimalist production aesthetic to a track list full of dark, sarcastic, self-immolating songs. (In some people’s eyes, In Utero is a more concise suicide note than the one that accompanied Cobain’s death.) The suits at Geffen famously rejected the album as “unlistenable” (according to Cobain, who may have been exaggerating), and it received a little polishing, but the album achieved the raw, aggressive sound that the band seemed to want. And poor Cobain was so good at writing hooks that the album enjoyed platinum success anyway, thanks to classic singles like “Heart-Shaped Box” and “All Apologies.”

2. David Milch, John From Cincinnati, (2007)

Over most of his time in show business, David Milch did one thing and did it well: grandiose, eloquent cop dramas. The guy broke in on Hill Street Blues, then worked his way up to co-creator of NYPD Blue, which set him for life. From there, he headed to HBO, patron saint of TV auteurs, to create the critically beloved Deadwood, which was killed off after three seasons in a dispute between HBO and Paramount. Milch then channeled all his pet obsessions, his penchant for obtuseness, and his bitterness at the Deadwood situation into the “surf noir” John From Cincinnati, which ended up being a loose retelling of the coming of Christ, shot through with esoteric philosophizing, opaque performances, and dialogue so convoluted that viewers had to listen three or four times to even figure out what was going on. John could be brilliant in patches, but it was too head-scratchingly strange for most viewers. Not even a small-but-rabid following or Milch’s insistence that it was all about how God wanted to prevent a genocide could curb viewer indifference.

3. Lou Reed, Metal Machine Music (1975)

While it isn’t the first solo album most Lou Reed fans reach for today, Sally Can’t Dance became Reed’s highest-charting disc in the U.S. The album’s tepid, laidback production—not to mention the notoriety of his previous albums—propelled it into the Top 10 in 1974, a success that perplexed the notoriously perverse songwriter. Frustrated by contractual pressure from his record label, and perhaps stricken with a bit of self-disgust at his own mainstream success, Reed responded with one of the most notorious albums in rock history, 1975’s Metal Machine Music—four sides of fussed-over distortion, reverb, and sonic unpleasantness. And while MMM’s freeform feedback-fest caused much critical groaning on its release, it remains, at least to some ears, far more rewarding than Sally Can’t Dance.


4. Dennis Hopper, The Last Movie (1971)

After the monumental commercial and critical success of Easy Rider, Dennis Hopper earned the leverage to do pretty much anything he wanted. Turns out he wanted to disappear into Peru and make a Jean-Luc Godard/Alejandro Jodorowsky-inspired experiment called The Last Movie, whose chilly reception and fleeting release turned Hopper into a drug-devouring Hollywood exile. Hopper stars as a stuntman named Kansas who, after shooting a difficult Western about Billy The Kid, decides to stick around in Peru. He eventually ends up looking for gold, then gets swept up in the madness of some locals who, in imitation of their recent Hollywood visitors, have created wooden cameras and boom mics to “shoot” their own movie starring Hopper. Not afraid to go meta or political, Hopper filled the film with distancing touches and blunt critiques of First World greed. “Scene missing” cards appear alongside images of hands pulling shots into focus. Twelve minutes into the film, we’re given a screen reading, “A Film By Dennis Hopper”; it’s another 13 minutes before the title appears, followed by lots of scenes of corrupt Americans living the high life on the backs of the locals. The messages look stoner-obvious, the fractured chronology is confusing, and the final stretches dip into hallucinatory madness, but The Last Movie’s disgust with the very idea of making movies and with movie-made myths is kind of fascinating anyway, even if it’s pretty easy to see why it never found an Easy Rider-sized audience.

5. Ken and Roberta Williams, Phantasmagoria (1995)

In the ’80s and ’90s, one of the few legitimately dominant computer game companies was Sierra On-Line, and that dominance came almost entirely from one husband-wife team: Ken and Roberta Williams. Ken programmed Roberta’s design for the family-friendly fairy-tale riff King’s Quest and managed to make it the first game in the “graphic adventure” genre to use animated sprites. Roberta continued to design every game in the wildly popular series, but she always seemed to carry a yearning to diversify. So in the mid-’90s she launched Phantasmagoria, her attempt to do a game as different as possible from the cartoony King’s Quest games. Phantasmagoria was a dark, often needlessly violent horror tale with borderline misogynistic overtones and a story all but plagiarized from Stephen King. Unlike the animated King’s Quest games, the entire game was done in then-popular full-motion video. In spite of kind reviews and big sales, Phantasmagoria became an afterthought at year-end awards, and genre enthusiasts rarely play it today. By the end of the decade, Roberta Williams retired, and graphic adventures largely died as an industry concern.

6. Robert Altman, Brewster McCloud (1970)

Robert Altman was never exactly a mainstream filmmaker, but something about his 1970 anti-war comedy M*A*S*H really clicked with audiences, and people eagerly awaited the next movie from a director with such a unique comic voice and a knack for reaching the younger generation. They didn’t have to wait long: Altman had another film in the pipeline, Brewster McCloud, starring Bud Cort as an eccentric young man who lives in the Houston Astrodome and dreams of flying. Brewster McCloud is every bit as shaggy and irreverent as M*A*S*H, but lacks the recognizable milieu and episodic plot of the earlier film, which left audiences more baffled than galvanized. And MGM didn’t do the movie any favors when they chose to première it at a big party in the Astrodome, attended by Houston locals (who weren’t exactly on Altman’s quirky wavelength) and the national media (who complained that Altman’s overlapping dialogue was impossible to hear inside the cavernous arena). Brewster McCloud got labeled a misfire before it even left the chamber, and Altman’s days as a crowd-pleasing studio darling were effectively over less than six months after they began.

7. Kanye West, 808s And Heartbreak (2008)

By the time he released his fourth album, Kanye West had gone from little-known producer to legitimate rap superstar: His previous album, Graduation, won three Grammys and went double platinum. But West had also made a career out of controversial statements, bizarre gestures, and critic- and audience-flummoxing moves, and 808s And Heartbreak was a doozy. Not only did it depart completely from his usual style, 808s wasn’t even a hip-hop record. Crammed with smooth melodies, R&B-style synth drums, and sung (well, Auto-Tuned) vocals about love and loss, it sounded like nothing he or anyone else had ever done. It instantly became, by mere virtue of its weirdness, the most talked-about album of the year.


8. Neil Young, Time Fades Away (1973)

Neil Young famously observed in the liner notes of 1977’s Decade that his hit “Heart Of Gold” put him “in the middle of the road” and “traveling there soon became a bore, so I headed for the ditch.” Time Fades Away marked the moment where Young grabbed the wheel of his thriving career and careened into a years-long detour from the mainstream. Recorded during a mammoth 62-date arena tour launched in the wake of Harvest, the bestselling album of 1972 and source for “Heart Of Gold,” 1973’s Time Fades Away featured songs that were pitch-black, half-written, and barely rehearsed—the antithesis of the well-crafted, country-ish folk songs that made Young a superstar. While Harvest fit comfortably with the music Young made with Crosby, Stills, Nash & Young, Time Fades Away is a raw document of Young’s grief and guilt over the heroin-related death of Crazy Horse guitarist Danny Whitten, as well as an early indicator of the even more abrupt stylistic shakeups he’d make later in his career. (Trans, anyone?) Young later called Time Fades Away his worst album—a distinction it doesn’t deserve, but a likely explanation for why it’s never been officially released on CD.


9. Steven Soderbergh, Kafka (1991)

After winning the Palme d’Or and establishing the commercial viability of independent filmmaking his first time at bat—“I guess it’s all downhill from here,” he famously quipped at the time—Steven Soderbergh was able to write his own ticket for his second movie. Rather than serving up More Sex, More Lies, More Videotape, however, he opted to tackle a notoriously difficult script by then-unproduced screenwriter Lem Dobbs, one that placed Franz Kafka at the center of a malevolent web of increasingly obscure intrigue. Aping the stark, shadowy monochrome look of German Expressionism, and devoid of the nuanced character studies that helped audiences connect with Soderbergh’s breakout debut, Kafka ultimately isn’t a very good film. But it also signaled Soderbergh as an adventurous, mercurial talent who had no interest in repeating himself. He’s confirmed that over and over again in the years since, by following up popular successes like Erin Brockovich and Ocean’s Eleven with alienating experiments like Full Frontal and The Good German.

10. The Get Up Kids, On A Wire (2002)

Before Fall Out Boy was a twinkle in Pete Wentz’s eye and Jimmy Eat World blew up around “The Middle,” The Get Up Kids released their second album, Something To Write Home About. And with that, they temporarily became the biggest thing going in emo, and helped Vagrant Records do what it did with bands like Dashboard Confessional and Saves The Day. But while the sound and style they helped foster was blowing up around them, The Get Up Kids turned their backs on it all with 2002’s muted On A Wire, which traded pop-punk anthems for Scott Litt production, campfire songs, and the kind of maturity greeted by lots of folded arms at shows. The intentional finger given to the band’s past was confirmed a few years later in an Alternative Press oral history that included bassist Rob Pope admitting, “We didn’t want to be the ‘emo’ poster boys,” while keyboardist James Dewees saw the writing on the wall: “I felt like we were committing career suicide.” That’s more or less what happened: On A Wire flopped, and fewer fans were around to hear the band rock out more on the follow-up, Guilt Show, GUK’s swan song. (Its temporary swan song, at least; the band recently reunited.)


11. Tom Patchett and Jay Tarses, Buffalo Bill (1983-1984)

Tom Patchett and Jay Tarses spent their careers before Buffalo Bill working at the MTM sitcom factory, a production studio known for its warm-hearted, caring shows about witty, urbane professionals. The two cut their teeth on The Bob Newhart Show, and the push-and-pull between their darker sensibilities and that show’s typical MTM milieu created the famed surreality of the show’s middle seasons. After leaving MTM, though, Patchett and Tarses were given carte blanche by a struggling NBC, and they followed those darker sensibilities until they created Buffalo Bill, a Dabney Coleman vehicle about an egotistical asshole of a talk-show host. In today’s TV-comedy landscape, it would fit just fine, but in the early ’80s, viewers tuned out in droves, in spite of the show’s awards nominations and critical acclaim. Patchett and Tarses’ partnership broke up acrimoniously after Bill went off the air after two short seasons, but it remains one of the few TV shows genuinely ahead of its time.


12. Radiohead, Kid A (2000)

After the smashing success of Pablo Honey and The Bends, Radiohead backlashed against alt-rock pigeonholing with OK Computer. That turned out to be a smashing success as well. Never much of a rock star, Thom Yorke was pretty burnt out by the spotlight, suffering from depression, lashing out at the media, and getting completely sick of rock music—and the melodies, harmonies, and choruses that went along with it. So Kid A did what OK Computer wouldn’t: eschewed singles, music videos, guitars, coherent lyrics, and anything else fans might want or expect. Layering electronics atop electronica, indulging in ambience, sprinkling in orchestration and noise-jazz, dabbling in nontraditional instruments (hey, is that the Ondes Martenot?), and picking lyrics out of a hat, Radiohead strung together musical abstractions and passed it off as a pop album. Justifying renewed faith in music fans worldwide, Kid A still entered the charts at No. 1 on three continents and was nominated for an Album Of The Year Grammy.


13. Stephen King, Different Seasons (1982)

In the afterword to Different Seasons, Stephen King describes how his first agent warned him of the dangers of being typecast as a horror writer; years later, when he decided to publish Seasons, he had to deal with objections to breaking that type. In the early ’80s, King had yet to reach his peak fame as the Master Of The Macabre, but he was well on his way with novels like ’Salem’s Lot and The Shining. Different Seasons offers a different kind of storytelling: four novellas, only one of which has the kind of supernatural horror that made King famous. Two of these novellas, “Rita Hayworth And Shawshank Redemption” and “The Body” aren’t horror at all, but “Apt Pupil” was the one that really put readers’ teeth on edge. The tale of a kid’s obsession with the Nazi next door is by definition frightening, but it’s also off-putting and vicious in ways King rarely tried, full of gassed hobos and childish sexual fantasies. These days, Seasons is just further proof of King’s popular appeal. All three of its non-supernatural sections have been adapted into films, and in the years since its publication, King has never been reluctant to try new things. But it came as a shock to readers at the time, like getting anchovies on a birthday cake.

[pagebreak]14. Mos Def, The New Danger (2004)

Black Star’s 1998 manifesto Mos Def And Talib Kweli Are Black Star and Mos Def’s 1999 solo debut Black On Both Sides made the rapper/actor/activist a hero to a generation of college kids and backpackers nostalgic for the glory days of The Native Tongues. Mos Def looked primed for greatness until a thriving acting career began to monopolize his time, and a dodgy-sounding rock project (to be called Black Jack Johnson) threatened to derail his music career. Def returned in 2004 with The New Danger, a Frankenstein monster of an album that combined tracks from the aborted Jack Johnson sessions with new hip-hop tracks steeped in paranoia. “The Rape Over” made longtime fans queasy/uneasy with lyrics about how a “tall Israeli” and “quasi-homosexual” were running hip-hop. (The track was mysteriously pulled from later printings.) The New Danger was a dark, uncertain album for a dark, uncertain era, and it left early fans wondering what happened to the idealism and warmth of Def’s early work.


15. Martin Scorsese, New York, New York (1977)

Martin Scorsese has made a career out of defying expectations, but even longtime fans were a little surprised when Scorsese followed up his iconic 1976 masterpiece Taxi Driver with a musical. True, 1977’s New York, New York owed as much to John Cassavetes as Arthur Freed, and it featured Robert De Niro at his most abrasive and off-putting (no small feat, considering his oeuvre), but it nevertheless belonged to a moribund genre that Scorsese and his fellow cinematic mavericks were supposed to have helped kill. New York, New York was gloriously, maddeningly representative of an age when auteurs were free to let their marauding ids lead them down all kinds of dark alleys.

16. Michael Cimino, Heaven’s Gate (1980)

Also representative of that age: Michael Cimino’s notorious 1980 revisionist Western Heaven’s Gate. The left-field success of The Deer Hunter afforded the famously prickly, indulgent director the power and clout to get financing for a defiantly non-commercial epic about brutal class struggles in 19th-century Wyoming. The film’s budget quickly spiraled, along with its running time and scope. Cimino ultimately turned in a rough cut that ran more than five hours, cost more than $40 million, and almost single-handedly destroyed United Artists. A messy, sprawling, overreaching film whose merits have been angrily contested over the past three decades, Heaven’s Gate confirmed Cimino’s status as an auteur with a strong, unique vision, while killing his reputation as a guy who could get films made.

17. Alice Sebold, The Almost Moon (2007)

Alice Sebold’s first novel, The Lovely Bones, was an instant mega-bestseller, widely purchased and widely praised for its lyrical language and strange, melancholy sweetness. For a story about a raped, murdered teenager who quietly watches the aftermath of her death from the afterlife, it felt oddly comforting and nurturing, with an overall feeling that no matter how bad life gets, there’s something better—and non-religious, and non-judgmental—waiting in the great beyond. Which may be why so many people were shocked five years later by Sebold’s follow-up, The Almost Moon. Written in a blunter style and about blunter topics, it follows a shell-shocked woman who kills her abusive mother, then embarks on a series of increasingly unlikely, grotesque decisions. It was as if Sebold had left heaven behind in order to concentrate on that “just how bad life can get” part. Granted, plenty of great literature follows that theme, but Almost Moon’s muddled story and even more muddled first-person narrator—who seemed to have no idea why she was dragging readers through such muck—didn’t invite sympathy, or even sustained interest.


18. N.W.A, EFIL4ZAGGIN (1991)

After rapper/chief-ghostwriter Ice Cube left, N.W.A. faced a dilemma, then a conundrum, then a big question: What do you do for a follow-up when you’ve shocked the world, transformed pop music, and lost one of your key voices? N.W.A.’s answer was to plunge even deeper into the shock, sex, and violence of its classic debut Straight Outta Compton, while eschewing much of the pop slickness that characterized Dr. Dre’s earlier production. EFIL4ZAGGIN (a.k.a. NIGGAZ4LIFE) took N.W.A.’s nihilistic ethos as far as it could possibly go, so it’s probably for the best that the most dangerous group in America disbanded soon after the album’s release.


19. Ben Folds Five, The Unauthorized Biography Of Reinhold Messner (1999)

With its breakthrough album Whatever And Ever Amen, The Ben Folds Five fused the classic piano-based songcraft of Joe Jackson and Todd Rundgren with the smartass sarcasm of Generation X. Folds quickly developed a reputation as a piano-pounding jokester, but there was always melancholy just under the surface. Folds and company’s brooding follow-up, The Unauthorized Biography Of Reinhold Messner, wore its rough edges proudly. It’s an intentionally messy album that veers from tortured self-reflection (“Mess”) to strangely moving experimentation (“Your Most Valuable Possession,” a song built around a half-lucid answering-machine message left by Folds’ father) to goofy toss-offs (“Your Redneck Past”). Though it failed to live up to its predecessors’ sales, Folds clearly has a soft spot for it; The trio recently reunited to perform the album in its entirety for MySpace’s “Front To Back” series.


20. The Monkees, Head (1968)

1968 found The Monkees’ career at a critical juncture. Auditioned and assembled to star in a Beatles-inspired TV show by producers Bert Schneider and Bob Rafelson, the cobbled-together band champed at the bit for more creative control over its work. By ’68, The Monkees had wrestled some of the power away from their puppetmasters, only to watch their show get canceled. And though they scored a hit in March with “Valleri,” the boys weren’t exactly burning up the charts the way they used to. The backlash kicked in hard, as old fans abandoned them for acts without the taint of the pop-factory assembly line. (Like, you know, The Lemon Pipers and 1910 Fruitgum Company, man.) The solution: a major motion picture directed by Rafelson—who co-penned the script with Jack Nicholson, a B-movie actor looking to establish a screenwriting career—that would be so weird and self-deprecating that the public would be shocked into embracing The Monkees all over again. The film opens with the group apparently attempting suicide, then repeatedly mocks the idea of the band as a product—in one scene, they play flakes in a dandruff commercial—between a rambling, seemingly stream-of-consciousness parody of whatever occurred to them. The movie flopped when released in November 1968, but these days, it’s a pretty fascinating curio, albeit one without even a fraction of A Hard Day’s Night’s timeless appeal. Winning moments aside, The Monkees remained an imitation to the end.

21. Fleetwood Mac, Tusk (1979)

While not exactly abrasive, Tusk was certainly jarring to many of Fleetwood Mac’s millions of fans, most of whom had been waiting two years for the follow-up to the hit-laden phenomenon of Rumours. Allegedly inspired by the experimentation of punk and new wave—although more believably the result of way too much cocaine and way too high a recording budget—Lindsey Buckingham spiked Tusk’s stark, dreamy rock with annoyingly bizarre compositions like “The Ledge” and “That’s Enough For Me,” the jerky, shrill “Not That Funny,” and the drifting disconnectedness of “That’s All For Everyone.” As an artistic statement, it was a brave one for the Mac to take, and it stands as one hell of a curveball from a band that never gets enough props for its edginess.


22. Orchestral Manoeuvres In The Dark, Dazzle Ships (1983)

“If You Leave,” OMD’s contribution to the soundtrack to the late John Hughes’ Pretty In Pink, is doubtlessly the band’s signature song. But its 1981 album Architecture & Morality was its breakthrough, selling millions of copies and putting the synth-pop group on the map in its native England. But rather than continuing that arc of increasingly palatable new wave, OMD chased Architecture with 1983’s Dazzle Ships, a disc seemingly pieced together out of eerie samples, prickly static, and a phalanx of malfunctioning factory robots. The challenging, often puzzling album was coolly received on its release, which led to the band’s headfirst leap into the pure teen pop of “If You Leave”—but Dazzle Ships has had a well-deserved resurgence in popularity since its re-release in 2008.


23. John Boorman, Zardoz (1974)

It’s an old story: A giant stone head flies across the countryside, dispensing arms and ammo to the locals (who are dressed in red underwear and bandoliers), and spouting off about the glory of guns and the evil of the penis. Sean Connery hitches a ride in the head, shoots a man who looks suspiciously like the Peculiar Purple Pieman Of Porcupine Peak, and manages to sneak into a city of ennui filled with craft-fair-obsessed immortals. And then things get weird. John Boorman’s Zardoz is a fascinating failure, a bold narrative vision that manages to be simultaneously breathtaking, pretentious, and achingly dull. What’s even more impressive is that the movie was Boorman’s direct follow-up to the hugely influential Deliverance, a naturalistic thriller typified by its straightforward storytelling and lack of ostentation. The contrast could hardly be starker, and it does Zardoz, a movie that dies the moment an audience member starts to snicker, no favors. (Not that Boorman cared; his follow-up to Zardoz was Exorcist II: The Heretic, which does to audience expectations what Godzilla did to Tokyo.)

24. Thomas Pynchon, Vineland (1990)

Thomas Pynchon’s 1973 novel Gravity’s Rainbow never became a popular success; like most of his work, it’s too dense and complex to find a mainstream audience. But it was a huge critical success, and it went on to become one of the signature novels of the 1970s. Then, nothing. Not for 17 years would the mysterious Pynchon produce another work of long fiction, and when it arrived, many of the same critics who had so firmly embraced Gravity’s Rainbow as the work of a serious man of letters decried Vineland as a deliberately ludicrous, intentionally unserious novel. Going from Rainbow’s World War II setting to the ’80-era ninjas, potheads, and Trekkies of Vineland infuriated critics who never much cared for Pynchon’s pop-culture obsessions and wild sense of humor. As a result, they tended to minimize or ignore the book’s many virtues—a pattern that repeated itself with the recent Against The Day and Inherent Vice.


25. John Lennon, John Lennon/Plastic Ono Band (1970)

In case he hadn’t already made it abundantly clear on his savage 1970 solo debut John Lennon/Plastic Ono Band, John Lennon explicitly stated his rejection of The Beatles and ’60s idealism on the album’s penultimate song “God,” declaring, “The dream is over.” But for anyone paying attention, the dream ended with the doom-laden church bells that open “Mother,” an uncomfortably intimate track that ends with Lennon’s screaming pleas for his parents not to abandon him. In contrast with The Beatles’ lushly reassuring swan song Abbey Road, the bone-dry Plastic Ono Band hits hard with unrelentingly grimness, stripping away Lennon’s superstar image, one incredibly fucked-up layer at a time. Lennon essentially committed his primal-scream therapy sessions to tape, consciously demolishing his hero status in the process.

26. Walter Wangerin, Jr., The Book Of Sorrows (1985)

Walter Wangerin, Jr.’s 1978 novel The Book Of The Dun Cow is a strange but terrific fable, brimming with fantasy tropes and religious metaphor, but able to stand on its own either as a conventional fantasy novel or an allegory about faith, courage, and sacrifice. It won the National Book Award and The New York Times declared it the best children’s book of the year, but it isn’t really for children, in spite of its talking-animal cast and broad good-vs.-evil story. In the book, a rooster struggles with his pride and weakness while defending his people from a grimly bloody, murderous invasion. It’s Animal Farm on a cosmic scale, written with respect both for the mundane details of animal life and the Biblical big picture. In the end, victory is hard-won and full of lessons about pain and grief. In the utterly inexplicable 1985 sequel, The Book Of Sorrows, Wangerin focuses solely on grief rather than victory, as the survivors of the first book basically give into despair and destroy themselves over hundreds of agonizingly pointless pages that undo every hard-won victory from the first film. Dun Cow reads like an act of faith; the follow-up is an act of hateful nihilism.


27. Weezer, Pinkerton (1996)

In 2009, it’s common knowledge that Rivers Cuomo is a weirdo, but in 1996, the world only knew him as the man behind some inescapable hits from Weezer’s 1994 debut. The world’s first glance into Cuomo’s eccentric, twisted psyche arrived with 1996’s Pinkerton, which clouded its predecessor’s sunny power-pop with deep-seated angst. Full of contradiction, it simultaneously evokes longing (“Across The Sea,” “Falling For You,” “Butterfly,” “The Good Life”) and emotional lethargy (“Tired Of Sex,” “Why Bother?”). For all of its darkness, Pinkerton still had plenty of hooks, but its darkness turned off the casual fans who tuned in during “Buddy Holly.” As such, it sold poorly upon its release, and Weezer essentially broke up after touring for it. But Pinkerton had legs, becoming a fan favorite in the decade after its release—a reputation solidified by Weezer’s string of sub-par albums following its reformation in 2000.