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The Best De La Soul Songs You’ve Never Heard

Their ten greatest non-hits

De La Soul was one of the great bands of hip-hop’s golden age of the late 1980s and early ‘90s. Mixing smarts with musicality, humor with depth, the Long Island trio of Posdnuos, Dave (formerly “Trugoy the Dove”) and Maseo melded genres on their groundbreaking 1989 debut, 3 Feet High and Rising — sampling Johnny Cash, Steely Dan, Billy Joel, Barry White and Hall & Oates. From there, De La went on a journey, expanding and refining its sound but never losing the thoughtfulness and love of a good hook that had been there from the start.

Unfortunately, in the streaming age, it’s damn hard to hear the band’s brilliance. As De La Soul has mentioned in recent interviews, the group’s old contracts didn’t cover digital releases, and so their songs’ copious amounts of sampling became a legal nightmare when the music industry entered the Spotify era. As a result, their catalogue isn’t as well-known as it should be, new generations of hip-hop heads unaware of a group that held its own against contemporaries like Public Enemy and the Beastie Boys, to name just two bands who were big fans. In fact, these days De La Soul is probably more famous for guesting on Gorillaz’s monster 2005 hit “Feel Good Inc.” than for any of its own material.

In honor of And the Anonymous Nobody, De La’s first album in 12 years, let’s salute the deep cuts of a trailblazing trio.

“Ghetto Thang” (1989)

When De La Soul dropped the dazzling 3 Feet High and Rising, the only knock on it was that the album was too hippie-dippy positive, as if hip-hop music had to adhere to some hyper-masculine idea of hardness or reflect some ugly vision of the poor black inner city. Forgetting for a minute how racist and narrow-minded that thinking is, the truth is that 3 Feet High actually touched on social commentary. “Ghetto Thang” is a deft, slow-burn look at the problems plaguing African-Americans’ impoverished communities — addiction, violence, disenfranchisement — while refusing to use those as excuses when individuals make bad choices.

“Oodles of Os” (1991)

The opening cut off De La Soul Is Dead marks a clear break from 3 Feet High and Rising’s Day-Glo sunniness. Accentuated by a slippery bass line from Tom Waits’ “Diamonds on My Windshield,” “Oodles of Os” is a jazzy cocktail in keeping with the bebop adoration that was going on in hip-hop at the time. (The track wouldn’t have been out of place on contemporary albums from A Tribe Called Quest or Digable Planets.) But what was the “Os” of the title? “That was something silly that Dave came up with,” Pos said in 2009. “What’s cool about the group is not knowing what your friend is talking about sometimes. At the end of the day, I just interpreted it as making a song about stuff that ended in Os.”

“My Brother’s a Basehead” (1991)

Hip-hop in the early ‘90s saw a shift toward drug tales, as rappers documented their experiences dealing on the street. In response, De La Soul offered “My Brother’s a Basehead,” in which Posdnuos chronicles his anger at a sibling for falling into addiction. This wasn’t fiction: He was writing about his older brother Tyrone — who’s now been sober for seven years. Sampling everything from the Doors to “Hang on Sloopy,” and incorporating a segue in which the song’s characters stop off at church, “Basehead” obviously lacks the trio’s usual playful sense of humor. In its place, Pos bitterly recounts the close bond he and Tyrone once shared, resigned to writing off his brother, who seemed beyond saving at the time.

“Afro Connections at a Hi 5 (In the Eyes of the Hoodlum)” (1991)

“This is dedicated to all those hardcore acts,” Posdnuos announces at the start of “Afro Connections,” a diss track that takes aim at gangster rap’s macho bullshit. Because this is De La Soul, though, the song doesn’t sound that gangster-y — but it is funny, mockingly taking the piss out of the genre’s over-the-top braggadocio. (Sample boast: “Now I hold my crotch / ‘Cuz I’m top-notch / I run amok Sasquatch / And I like to eat live crab / I’ve got five beepers, you scab.”) But underneath the jabs are great rhymes and a principled disgust at an art form being corrupted by wannabe thugs.

“I Am I Be” (1993)

The apex of De La’s dabblings with jazz, this Buhloone Mindstate cut is powerfully introspective, its weariness evoking both sadness but also resilience. “I Am I Be” is the band’s state-of-the-union address, and the news isn’t good. Posdnuos is disillusioned by the music industry, anxious about fatherhood and angered by the fracturing of the so-called Native Tongues collective. (“Some tongues who lied / And said ‘We’ll be natives to the end,’” he sings. “Nowadays, we don’t even speak / I guess we got our own life to live / Or is it because we want our own kingdom to rule?”) Featuring exquisite horns played by three legends (Pee Wee Ellis, Maceo Parker and Fred Wesley), this soulful ballad tries to find a little light amidst the gray skies. But all you’ll feel is the blues.

“In the Woods” (1993)

Buhloone Mindstate found De La Soul inviting rapper Shortie No Mass to join in on a few tracks, giving the band a smart female voice that struck a blow for inclusiveness in a genre that was very male-centric. The highlight of their collaboration, “In the Woods,” drops sharp rhymes over a pounding sample of Lonnie Smith’s cover of “Spinning Wheel.” On the mic, Pos, Dave and Shortie attack everything from racism to sexism to hip-hop’s penchant for mistaking “hardness” for talent or lyrical depth. (On that last point, Pos brilliantly drew a line in the sand: “Catch me breathin’ on planes where the gangstas outdated / Fuck being hard, Posdnuos is complicated.”) “In the Woods” should have been an anthem for rap’s enlightened brethren — instead, it’s a slept-on classic.

“Brakes” (1996)

After making their first three albums with visionary producer Prince Paul, De La Soul set out on their own with Stakes Is High, preferring a stripped-down, almost resigned sound. (The sense of anger and futility is everywhere on the record: There’s even a snippet of a man using racist language to describe why he hates rap music.) But despite that air of gloom, the trio double down in their belief that true hip-hop can conquer all. “Brakes” reminisces about De La’s early days while looking around at the woes that bring people down: violence, crime, disease. Ultimately, though, this is an optimistic song — despite its muted melody, the rappers paint themselves as defiant survivors who haven’t forgotten that one great song can make life a little more bearable.

“U Can Do (Life)” (2000)

2000’s Mosaic Thump was meant to be the first installment in a trilogy of records, known collectively as Art Official Intelligence, which would reassert De La’s place in the hip-hop firmament after years away from the game. In the end, the group only released two discs, both of which failed to return the band to its former glory. No matter: This opening track is where Pos and Dave remind listeners how long they’ve been in the game and what they stand for. (“I maintain like a old jazz singer,” Dave declares, slamming flash-in-the-pan newcomers.) Channeling the 1970s R&B they love, De La Soul ride the smooth, funky groove to salute what really matters: taking care of your family, maintaining your integrity, ignoring the haters.

“My Writes” (2000)

Mosaic Thump featured plenty of guest stars, everyone from Chaka Khan to the Beastie Boys to Busta Rhymes. On “My Writes,” De La recruited Tha Alkaholiks and Xzibit to join in on a song in which the elder statesmen let the new bloods know who’s running this thing. The low-key track succeeds in getting you to bob your head, while the chorus brags, “What you know about my writes? / What you know about what’s weak, what’s tight?” It’s probably the only hip-hop song that gives a shout-out to flossing, and Pos gets a few laughs amid his snarling verses, announcing, “I’m claimin’ these tunes / In this we’ll stay down like seats found in sorority bathrooms.”

“Simply” (2001)

Sometimes, a great rap song is born from finding the craziest, most obscure sample. And then other times, it’s cool to just rock to Paul McCartney’s Christmas hit “Wonderful Christmastime.” “Simply” belongs in the latter category. This Bionix track is nothing more than celebrating good times: The guys hang out, try to pick up some ladies, hit the dance floor, and pledge allegiance to old-school hip-hop. The sample’s nostalgic pull meshes perfectly with the song’s acknowledgement that, once you become a grownup with kids and responsibilities, it’s damn hard to find a little downtime just for yourself. No wonder that “Simply” sounds positively chill: These 30-something dudes are happy to just kick back and take it easy while they can.

Tim Grierson is one-half of The New Republic’s film column Grierson and Leitch. He is also a frequent contributor to Rolling Stone and Vulture as well as the author of six books, including a biography of Public Enemy.