Some artists just have it: the ability to lead us around by the nose. We happily let them do anything; they have passports to go anywhere, try whatever crazy idea pops into their head. Wear a swan dress to the Oscars? Sure, BjÃ¶rk. Release four albums in 16 years without losing any fans? Go ahead, Fiona! Cover yourself in stage blood, roll over live audiences in an enormous hamster ball, and make drugged-out duets with Ke$ha? By all means, Wayne Coyne.
They aren’t rule-breakers, exactly. People who set out to break rules have to be aware of them in the first place. For this rarefied bunch, it seems simply that the rules don’t apply. We tend to hold them in awe and fascination; they reward us by surprising us. They are artists who do whatever the $%&@ they want. — Jayson Greene
Why She Belongs: Two things that the recent release of her brazenly confessional record The Idler Wheelâ€¦ — her fourth in sixteen years — have made clear: no one tells Fiona Apple what to do, or when to do it. But the seven-year wait for the elegantly sparse The Idler Wheel was well worth it: from the raw vocal tour de force "Daredevil" to the wry, bittersweet wit of "Werewolf," Apple's fierce, unique, wild talents have only grown more sharply toned with time.
Most Fearless Moment: Apple's infamous acceptance speech at the 1997 VMAS ("This world is bullshit") caught her flack at the time, but it perfectly captures the independent-minded, plainspoken audacity of her subsequent career. — Lindsay Zoladz
Why She Belongs: Badu started her career as a fully formed icon of the neo-soul movement, all cocoa butter, Billie Holiday impressions and Afro-print wrap skirts. Her debut, Baduizm, shipped to record stores having already gone platinum. Breaks between albums became increasingly long; albums became increasingly inscrutable. She tweeted through her last pregnancy and named the baby Mars. She has endorsed Palestine and started a non-profit organization to support the arts in South Dallas. At no point has she ever tried to replicate her early success or seemed overshadowed by it, either.
Most Fearless Moment: No doubt some will say that this goes to the video for "Window Seat," where she stripped naked while walking through Dallas's Dealy Plaza. But public nudity makes her about as fearless as the common American fraternity brother. Really, the moment goes to 2008's New Amerykah: Part One (4th World War), where, after five years of being out of the public eyes, she decided it might be smart to release an hour of paranoid funk music replete with samples of Louis Farrakhan. — Mike Powell
Why He Belongs: The Flaming Lips' mischievous majordomo refuses to acknowledge the line between experimentation (crowd-interaction pieces with boom boxes and iPods) and pop (inviting Ke$ha onto 2012's Heady Fwends). Whether making films in his backyard, walking on a festival crowd's hands while encased in a giant bubble, or gladly playing the band's fluke 1994 hit "She Don't Use Jelly" (he still likes it, damn it), he's rock's sagest goof, driven by an iron will.
Most Fearless Moment: Issuing 1997's Zaireeka as a four-CD set, all of whose discs are meant to be played simultaneously. — Michaelangelo Matos
Why He Belongs: Albarn could have gone on touring with (or as) Blur forever. Instead, he's invented the semi-fictional band Gorillaz, recorded with local musicians in Mali and Kinshasa, and formed an ongoing alliance with Fela Kuti's former drummer Tony Allen.
Most Fearless Moment: The rave kids who danced to Blur mocking them in "Girls & Boys" have to have been thrown for a loop by Albarn writing the score for a 2007 musical theatre piece based on Wu Ch'eng-en's 16th-century Chinese novel Journey to the West. — Douglas Wolk
Why She Belongs: Smith's explosive performances at CBGB's in the mid '70s set the template for American punk by spitting on the very idea that there could be a template for punk. Nearly four decades into her career, Smith's most recent endeavors — the award-winning memoir Just Kids, her typically unpredictable and wandering latest record Banga — show that her creativity still recognizes no boundaries.
Most Fearless Moment: Leaving New York City and stepping out of the spotlight at the height of her success to go raise a family (and record a couple deeply personal records, like 1988's Dream of Life) in Detroit with her late husband, Fred "Sonic" Smith. — Lindsay Zoladz
Why They Belong: Liars were the most creative and least compromising of the post-punk bands to revive the NYC scene in the early '00s. But their taut debut, They Threw Us All in a Trench and Stuck a Monument on Top, was just the first stop on Angus Andrew and co-founder Aaron Hemphill's journey of perpetual reinvention. Neither the dark techno vibes of the new WIXIW nor the path that led to it — from the noise-rock of They Were Wrong, So We Drowned into the percussive jungle of Drum's Not Dead and through a variety of mutated rock and pop forms on Liars and Sisterworld — could've been predicted, with Liars' only constant being a pervasive sense of dark disquiet.
Most Fearless Moment: They Threw Us All in a Trench made Liars one of NYC's most well-known club bands. But instead of building on their popularity, Andrew and Hemphill reworked the band's lineup and, two and a half years later, returned with their most uncommercial statement, They Were Wrong, So We Drowned, a brilliantly discordant, sometimes downright frightening melding of rock sounds, industrial textures and witchy themes. — Mike Wolf
Why He Belongs: The industrial genius/digital innovator had a very specific musical vision for Nine Inch Nails — and an uncompromising visual aesthetic — which he implemented with laser-guided focus. In later years, he flouted traditional label structure, gave away several albums for free, and then put NIN on hold to score films and form a new band, How to Destroy Angels.
Most Fearless Moment: 1999's The Fragile, a double album with atmospheric instrumentals a la Brian Eno and no overt mainstream moments. — Annie Zaleski
Why He Belongs: Although he's as established an icon as any in pop, the Purple One has long framed his career as a kind of insurrection — against genre lines ("When You Were Mine"), sexual orthodoxy ("Darling Nikki"), dumb-ass record execs (Chaos and Disorder), you name it. To immerse yourself in the pleasures of his wildly varied (yet consistently idiosyncratic) catalog is to wonder why so few big-thinkers have as much fun as Prince does.
Most Fearless Moment: His 1996 three-disc set Emancipation, on which he celebrated his break with Warner Bros. in typically counterintuitive style: with an inarguably gorgeous rendition of the early-'70s soul jam "Betcha By Golly, Wow." — Mikael Wood
Why She Belongs: The Icelandic singer-songwriter earns near-universal respect from all musical quarters. (A short list of collaborators: LFO, David Morales, the Brodsky Quartet, Timbaland, Matmos, Mike Patton, Zeena Parkins, Konono No. 1, Lightning Bolt.) She made an album dominated by laptops (2001's Vespertine), followed by an album of a cappella vocals (2004's Medulla), and then later an album that was also an app (2011's Biophilia). No one would blink an eye if her next album were all death metal.
Most Fearless Moment: Without a doubt, her "swan dress" at the Academy Awards in 2001. â€”Michaelangelo Matos
Why He Belongs: Nilsson was a singer-songwriter who leveraged his commercially viable stuff with stuff that was anything but — following two Top 10 singles, for example, with one whose chorus ends in "fuck you." He more or less refused to play live, though once agreed to a BBC television special on the condition he got to do things like "film himself sleeping in the audience of his own concert." He was both of the establishment and against it, an artist happy being marginally famous until being marginally famous meant doing things he didn't feel like doing. And when it came to that, he stopped doing things entirely — sad, in a way, but also inspiring, for however rare fame is, integrity's rarer.
Most Fearless Moment: In 1972, his album Nilsson Schmilsson went gold, and its centerpiece, "Without You," won a Grammy. He had never been more famous. A year later he released A Touch of Schmilsson in the Night, an irony-free collection of ballads that had been desperately out of fashion since World War II, recorded it London with a 39-piece string section. In an interview on New York's WNEW, he said he preferred the London studios in part because they got good drum sounds. (Touch doesn't have any drums on it.) Never has commercial suicide sounded so classy. — Mike Powell
Why He Belongs: Ornette's biggest selling point is that he never does the expected — even his first record was called Something Else!!!! — and he'd qualify on the strength of Free Jazz alone: More than 35 minutes of free improvisation, unheard of at the time.
Most Fearless Moment: He's worked with all sorts of unexpected collaborators, from Pat Metheny to Yoko Ono, but inviting his son Denardo Coleman to become his group's drummer with 1967's The Empty Foxhole was a jaw-dropper, mostly because Denardo was 10 years old at the time. — Douglas Wolk
Why He Belongs: Operating by his own rulebook from adolescence, Richard D. James has screwed with pretty much every electronic-dance subgenre in devil-may-care fashion. His "remixes" often sound nothing like the original tracks. His long absences between recordings post-'90s make his audience's hunger for anything at all that much more acute.
Most Fearless Moment: Playing a "DJ set" with sandpaper discs and sound effects provided by a blender during a Blast First Records showcase in New York, 1994. â€”Michaelangelo Matos