Trugoy the Dove of De La Soul’s 10 Essential Songs

David Jolicoeur, best known as the rapper Trugoy the Dove of the climate-shifting rap group De La Soul, weathered decades of industry shifts with acerbic wit, oblique rhyme styles and intense bouts of self-reflection that flew in the face of hip-hop’s boast-centric bottom line.

Jolicoeur, also known as “Plug Two” in the Long Island trio he helped found in 1988 with Kelvin Mercer (Posdnuos) and Vincent Mason (P.A. Pasemaster Mase) died on Sunday at 54, just weeks before the group’s songs, long absent from streaming services, will finally arrive on digital platforms.

De La Soul’s debut album, “3 Feet High and Rising,” from 1989, was nothing short of a sea change moment in the genre’s sound, fashion, attitude and aesthetic. As leading lights of the Native Tongues collective — a loose crew of fellow travelers that included Jungle Brothers, A Tribe Called Quest, Queen Latifah and Monie Love — De La’s baggy bohemian look would replace rap’s thick gold chains and sweatsuits with Afrocentric leather medallions and vintage patterns. It was Jolicoeur’s innovation to raid their dads’ closets for bell bottoms and straighten the legs, not to mention stylizing their asymmetrical haircuts.

De La Soul broke the Top 40 that year with the pop splash “Me, Myself and I” — for years the trio would reliably add “We hate this song!” when performing it live — but went on to become hip-hop royalty thanks to the emotional depth plumbed in tunes like “Tread Water” and “I Am I Be.”

Quirky production, introspective lyrics and its unorthodox look had De La Soul dubbed “alternative hip-hop,” a feel that would rapidly spawn similar-minded artists like the Pharcyde, Digable Planets, P.M. Dawn, Arrested Development and Dream Warriors. But over time, its legacy became less a recognizable “sound” and more a model for any rap act open to aesthetics and ideas that cut against the hardcore grain, like the Roots, the Fugees, Common, Black Star and eventually world-conquering artists like Kanye West and the Black Eyed Peas.

Here are 10 essential verses from an artist whose “Delacratic” attitude toward self-expression helped rewire hip-hop’s DNA.

De La Soul, “Plug Tunin’” (1988)

On its debut single, De La Soul introduced an abstract “new style of speak” that landed in the middle of the hard-edge Def Jam era like a prismatic fracturing of hip-hop, beat poetry and alien transmissions. On the first song the trio did as a group, Jolicoeur coolly raps like a Slinky tumbling down stairs, “Dazed at the sight of a method/Dive beneath the depth of a never-ending verse/Gasping and swallowing every last letter/Vocalized liquid holds the quench of your thirst.” As he told the author Brian Coleman of their lyrics at that time, “Maybe it was our warped character, but we didn’t really want people to understand it at all. Sometimes we were trying to make it difficult, because it would make people always want to know more.”

De La Soul, “Me, Myself and I” (1989)

De La Soul’s biggest hit was also De La Soul’s biggest albatross: The Day-Glo visuals around its single and video promptly burdened the group with the label “hip-hop hippies.” In a sad irony, Jolicoeur’s verses on “Me, Myself and I” were specifically about not being judged by his unconventional fashion choices. Borrowing the rhyme flow from “Black Is Black” by the Jungle Brothers, another Native Tongues crew, Jolicoeur opens the trio’s first and only Top 40 pop hit with a radical mix of exhaustion and self-questioning: “Mirror mirror on the wall/Tell me mirror, what is wrong?/Can it be my De La clothes/Or is it just my De La song?” “If some think that we have a hippie style and a hippie sound, that’s just fine,” Jolicoeur told Melody Maker in 1989. “But we’d be offended if it was said that we wanted to be hippies. We don’t. We just want to be ourselves.”

De La Soul, “Pass the Plugs” (1991)

The second De La album — sardonically titled “De La Soul Is Dead” — pushed back on the daisies and fluorescents with a sound that was a little more disillusioned and dark but still breezy. Taking the second verse of “Pass the Plugs,” Jolicoeur bemoans the industry panopticon of radio programmers, promoters and a record label that wanted more hit singles.

De La Soul, “Millie Pulled a Pistol on Santa” (1991)

The most lyrically and thematically intense song of De La Soul’s career, “Millie Pulled a Pistol on Santa” tells the story of a Brooklyn girl abused by her father — by the song’s end, she takes her revenge with the titular weapon as he works as a department store Kris Kringle. The story is narrated mainly by Mercer, who was channeling real-life emotions after finding out a friend was a survivor. However, in a masterful storytelling technique, Jolicoeur takes two verses as the doubting acquaintance who doesn’t believe the girl’s accusations.

Teenage Fanclub and De La Soul, “Fallin’” (1993)

Treating an entire song like one of its famous skits, De La play washed-up, once-successful rappers on this collaboration with the Scottish jangle-rock band Teenage Fanclub for the “Judgment Night” soundtrack — a weirdly prescient rock-meets-rap experiment. “We wouldn’t play ourselves to do something that was wack, but the way the concept plays itself out, it’s supposed to be wack,” Jolicoeur told Vibe in 1993. “The track is supposed to sound wack.” Instead, the group’s look at the other side of fame produced some of the most poignant verses of its career. Raps Jolicoeur, “I knew I blew the whole fandango/When the drum programmer wore a Kangol.”

De La Soul, “Ego Trippin’ (Part Two)” (1993)

On this single from De La Soul’s jazz-flecked third album, “Buhloone Mindstate,” Jolicoeur draws a sarcastic line between his group and contemporary hip-hop machismo and bragadoccio. “I change my pitch up, smack my bitch up, I never did it,” he raps, flipping a classic line from New York’s Ultramagnetic MC’s. “The flavor’s bein’ bought, but brothers ain’t gettin’ it.”

De La Soul, “Stakes Is High” (1996)

“Stakes Is High” was not just the evocative title to De La Soul’s fourth album. As Mason told Okayplayer, “I mean the whole energy around developing that record, it was a crucial place of not knowing if we was going to continue or we going to be forced to go get regular jobs and become common folk.” For the lead single and title track — produced by the emerging beatmaker Jay Dee, later known as J Dilla — Jolicoeur unleashes a torrential downpour of criticism deriding the state of mainstream hip-hop: “Sick of swole-head rappers with their sickenin’ raps/Clappers of gats, makin’ the whole sick world collapse.”

De La Soul, “Itzsoweezee (Hot)” (1996)

The last track recorded for “Stakes Is High,” though it ultimately became the album’s second single, was a rare solo turn for Jolicoeur. As Mafioso imagery began taking over hardcore New York rap, Jolicoeur popped the bubble with lines like “Why you acting all spicy and shiesty?/The only Italians you knew was Icees.”

Prince Paul featuring De La Soul, “More Than U Know” (1999)

Another prime example of Jolicoeur and Mercer’s storytelling abilities is this song from the producer Prince Paul’s wildly ambitious concept opera “A Prince Among Thieves.” Playing the role of a crack addict, Jolicoeur pulls the extended metaphor trick, rhyming about the drug as if it were a love interest: “I can’t refuse her, my denial’s a wish/Fell into her arm when I gave her a kiss.”

Gorillaz featuring De La Soul, “Feel Good Inc.” (2005)

This alterna-pop gem from Damon Albarn’s virtual cartoon crew ultimately became the biggest success story of De La Soul’s career, garnering the group its first and only Grammy. Known for a usually mellower delivery, Jolicoeur instead unleashes a barrage of high-octane bars: “Laughing gas these hazmats, fast cats/Lining ’em up like ass cracks/Play these ponies at the track.”