Nappy Roots
Poor Nappy Roots. The Kentucky quartet had that Southern-fried rap thing going, but appeared during a time when the South was, like, a hip-hop "aesthetic." Being lumped in as Southern 101 with Outkast (Speakerboxx/Love Below was just released at the time of this single), and the now-forgotten Bubba Sparxxx, made this fairly talented group feel a bit like a novelty.
UGK
While Tupac and Biggie were off dealing with West versus East beef, UGK just hung out down South all like, "What coasts?" Though it has a well-deserved spot in the legacy of rap music, the Underground Kingz had very little mainstream success — and the big win it did have was thanks to a foul-mouthed Jay Z verse. (Hey Jay, remember "Me give my heart to a woman / Not for nothin', never happen / I'll be forever mackin'"? Yeah. You said that, and no take-backsies.) And, while "International Player's Anthem" was the group's only track to (barely) chart on the Billboard Hot 100, it's "Big Pimpin'" that will always be UGK's trademark.
Sinéad O'Connor
Rip up one teensy-tiny picture of a pope, and poof! There goes your career. True, the last few years haven't been so kind to Sinéad, with the open letters, weird marriages, and unfortunate Twitter rants, but her first several albums were exquisite. (In fact, even her reggae album was surprisingly listenable and almost no one's reggae album is listenable.) Though some circles celebrate I Do Not Want What I Haven't Got as the ultimate eff-you album, O'Connor's legacy deserves more than that SNL mishap. Listen to "Troy," right now, and feel feelings. All of them.
Faith No More
Though Mike Patton has a cult following of his own (he's the Oingo Boingo Mr. Bungle guy, folks!) [Edit Note: Apparently, I confused Danny Elfman with Mike Patton for no real reason, except that I think I listened to both of their records a lot during the same era...?], Faith No More is now best remembered for the band's appearance as a super difficult Guitar Hero level. "Epic" charted impossibly high and did exceedingly well, and the metal-rap mash-up (hey, it was innovative back then) gained FNM a huge number of hard rock fans who didn't quite get its quirk or Patton's specific singing style. Well, at least the single will always go down as the worst/best karaoke option ever.
Butthole Surfers
For years, Gibby Haynes and Co. influenced the American punk scene, and, like early label mate Jello Biafra of Dead Kennedys, fused politics with aggression. Respected, disgusting, and wildly irreverent, the Surfers were favorites of Kim Gordon, Kurt Cobain, and even Beavis & Butt-head. And, then, "Pepper" came out, and suddenly the Surfers were faced with a massive radio hit. They were never able to replicate that success again — but they may not have wanted to.
The Verve
The first thing you should know about The Verve is that, as its Wikipedia page notes, this Britpop band is not to be confused with Michigan rock group The Verve Pipe. No, Richard Ashcroft's group is famous for "Bitter Sweet Symphony," which became both a chart-topping success and a legal nightmare. The song's infectious melody was based on an Andrew Loog Oldham Orchestra rendition of The Rolling Stones' song "The Last Time," and the band was forced to hand over copyright and royalties to Mick Jagger and Keith Richards, rendering its great hit actually a really giant financial disaster. After "Bitter Sweet Symphony," the band was nominated for a Grammy and had another hit with "The Drugs Don't Work," but it ultimately decided to call it quits in 1999. A series of reunions and breakups have followed in the 15 years since.
New Radicals
The most ironic thing about the New Radicals' "You Get What You Give" is that the feel-good hook completely obscured the song's theme of raging against consumerism, corporate greed, and celebrity culture. Instead, we only remember it now as the soundtrack for car commercials, which is part of the reason New Radicals' frontman Gregg Alexander dissolved the band after the song became a huge hit. The second single, "Someday We'll Know," is a beautiful ballad about love and loss, but it failed to match the success of "You Get What You Give." Also? He was super cute. Doesn't change anything, but it is a good thing to keep in your brain.
Imogen Heap
Though Imogen Heap has gone on to see relatively great success in her unique sonic niche (her Mi.Mo gloves are just now making waves in the tech world), the attention she received for her auto-tune opus "Hide and Seek" disappeared as fast as Marissa's sanity on The O.C. Jason Derulo brought it back in 2009's "Whatcha Say," but Heap's name never became as recognizable as it could've been. It's a shame, really, because her innovations and experimental approach to music making is shaping the top 40 we hear today.
Gary Numan
If the only thing you know about Gary Numan is that he's that odd, short fellow who really likes hanging out in his car, give his influential 1979 album The Pleasure Principle a listen. Following in the footsteps of Kraftwerk, it was one of the first mainstream rock albums to completely abandon guitars for synthesizers, helping to usher in the popularity of the synthpop genre in the early '80s. In fact, the bands he has influenced — Nine Inch Nails, Marilyn Manson, Ministry — have had more commercial success than Numan ever did. Check out "Me! I Disconnect from You" and "Down in the Park" from his earlier album with Tubeway Army, and Pleasure Principle's "Airlane" and "Metal."
Vangelis
Okay, this may be nitpicky, but Vangelis did the soundtrack to Blade Runner and that soundtrack absolutely rules. That is all.
Nancy Sinatra
"Boots" was far and away Sinatra's biggest hit, but fortunately, time has been kind to the woman with a very famous father. Her cheeky, slightly subversive lyrics have made her a go-to for both Quentin Tarantino and Lena Dunham, and fortunately, her other hits (like "Sugar Town") are finally reappearing as quirky anthems for Zooey Deschanel-style characters in flouncy dresses.
Deee-Lite
Look, "Groove Is In The Heart" is great. But, the psychedelic ode to '90s-club-kid positivity is such a wonderful relic of its time that the whole thing is like a delicious time capsule of an era before Michael Alig was a just-released felon. Lady Miss Kier had pipes and style, Dmitry and Towa Tei had productions chops — the only thing that held them back was personal discord. World Clique is a club classic, Infinity Within is a jam, and Dewdrops In The Garden would have been a surefire hit if it got some radio play. These are facts. Undisputed facts. But since this was the '90s, it is spelled "fax."
Digable Planets
Digable Planets was the unthreatening hip-hop for '90s college kids who wanted to enjoy their own "Nickel Bags of Funk" but couldn't get behind the aggressiveness of gangsta rap. Although they didn't exactly pioneer the genre, Digable Planets helped to spread the jazz-infused style developed by A Tribe Called Quest. The Planets were worthy successors and all had insect names, like Butterfly and Doodlebug.