Have pity on poor Boots Riley, trapped in an extra-testy January 2002 episode of Bill Maher’s Politically Incorrect, having raised a ruckus by saying the three most incendiary words a subversive rapper and (eventual) pop-surrealist filmmaker can possibly say: “I’m a communist.” Maher’s fellow guests this evening include a conservative activist, a soap opera star, and a comedian wearing a leather jacket; Mr. Soap Opera is especially incensed, squaring up like a sumo wrestler (as Mr. Leather Jacket observes) and demanding to know what Riley’s got against capitalism, anyway.

Cue two minutes of pointing and shouting. Don’t rappers benefit from capitalism? Didn’t communism already fail spectacularly? What about human nature? Until Maher, with maximum smugness, calls for “a capitalistic break” for commercials, Riley valiantly tries to hack through all this irate cross talk. And though it’s a losing battle, it is yet another vivid example of how hard and for how long he has fought to be heard and understood, no matter how hopeless the outcome, no matter how absurd the venue.

Boots Riley defending communism on _Politically Incorrect_ back in the day while Bill Maher is smug as fuck and stupid as always. pic.twitter.com/rLgwy5IoPY — GEOTRILL (@delmoi) July 24, 2018

That old clip went viral in July, the same month Riley, the leader of long-running and fiercely beloved Oakland rap group the Coup, finally saw the wide release of his dazzlingly bonkers directorial debut, Sorry to Bother You. Starring Lakeith Stanfield and Tessa Thompson, it is as vibrant and outlandish and singular a movie as 2018 has to offer, a ludicrous sociopolitical fable about telemarketing, union organizing, and the mythic power of using your “white voice” that blossoms, slowly and bizarrely, into a slapstick indictment of Silicon Valley–abetted slave labor. Yes, Mr. Soap Opera, this movie benefits from capitalism and yet spectacularly interrogates capitalism. It is a culmination of everything Riley has been saying and shouting and, most importantly, rapping for decades.

Riley had shown up on Politically Incorrect that day to promote and/or defend the Coup’s fourth album, Party Music, very famously set for a September 2001 release with a very infamous cover image of Riley and the Coup’s longtime DJ, Pam the Funkstress, blowing up the World Trade Center. (After the 9/11 attacks, the group’s label at the time changed the cover over Riley’s protestations.)

Party Music remains, due to that calamity, the Coup’s most famous record. But if Sorry to Bother You lit your head on fire, the ideal next step in your Boots Riley–led reeducation is their third full-length, Steal This Album. It was released on November 10, 1998; it turns 20 years old on Saturday. Paint a little picture of a birthday cake on a rock and throw it through a bank window. Flashier rap records came out in ’98—think OutKast’s Aquemini, or Jay-Z’s Vol. 2… Hard Knock Life, or Juvenile’s 400 Degreez, or The Miseducation of Lauryn Hill. But in typically singular fashion, the state-smashing provocations of Steal This Album have only grown more potent and necessary with time, which is both a great testament to Riley’s revolutionary vision and yet another profound indictment of the state.

The Coup started out as a trio (rounded out by rapper E-Roc, who eventually left the group in 1997) with a fairly explicit point of view, mixing aggressive Marxism with laid-back Bay Area bombast: Their first two albums were called Kill My Landlord (1993) and Genocide & Juice (’94). But Steal This Album was a revelation, the group reduced to the duo of rapper-producer Riley and DJ Pam the Funkstress, their rabble-rousing POV even sharper (from the title’s shout-out to ’60s counterculture hero Abbie Hoffman on down), their songs blooming into Homeric epics or party-starting anthems, or both.

Vocally, Riley has both the fiery, bully pulpit righteousness of Chuck D and the eccentric, trunk-rattling precision of fellow East Bay legends E-40 and Too Short; lyrically, the only thing more striking than his comedy is his tragicomedy. He can be very funny, and he can get very angry. “Cars & Shoes” is a rubbery bit of bubble funk with a Weird Al–worthy loopiness to it as Riley describes exactly how shitty his car is: “The seatbelt don’t work, just tie it ’round your waist / If you crash through the window just cover your face.” It’s too silly to be depressing, and as that deathtrap with a hole in the floorboards rumbles around Oakland, the song paints a sonic picture of the city every bit as vivid as what’s on-screen in Sorry to Bother You. Elsewhere, the catchiest, and funniest, and rudest track is called “Piss on Your Grave,” which features a mid-song skit set at Arlington National Cemetery so Riley can, uh, pay his respects to George Washington. Maybe don’t play that one for Mr. Soap Opera.

But most of Steal This Album breaks down the degradations of abject poverty in harsh, wrenching, uncomfortably vivid detail, its tone furious throughout and heart-wrenching when it has to be. The grim “Breathing Apparatus” is basically health care horrorcore: “My medical plan was to not get shot,” Riley raps, describing a hospital as a haunted house for the uninsured, with a call-and-response chorus all the more infectious for how clunky it looks on paper. Call: “I ain’t gon’ let ’em fuck with your breathing apparatus.” Response: “Please don’t let ’em fuck with my breathing apparatus.”

In “Busterismology,” Riley seeks revenge on his imperious old dirtbag of a McDonald’s manager for tricking him into giving up his unemployment benefits; the chorus, amid organ stabs and a sawing strings riff, is “When we start the revolution / All they probably do is snitch.” The deluxe-reissue track “What the Po-Pos Hate” is sublime and self-explanatory G-funk: “Shaking in their boots when we start to bust / They ain’t scared of rap music, they scared of us.” The most startling shift from light to dark comes when “The Repo Man Sings for You,” a goofy ode to the perils of TV repossession bolstered by monster-movie piano and a guest spot from fellow Oakland luminary Del the Funky Homosapien, dead-ends into “Underdogs,” a slo-mo bruiser that starts with a destitute woman shrieking I can’t take this shit no more and features some of Riley’s most lucid and upsetting writing:

Lights turned off and it’s the third month the rent is late

Thoughts of bein’ homeless, cryin’ till you hyperventilate

Despair permeates the air, sets in your ear

The kids play with that one toy they learned how to share

Comin’ home don’t never seem to be a celebration

Bills they piled up on the coffee table like they decoration

Big ol’ spoons of peanut butter, big-ass glass of water

Makes the hunger subside, save the real food for your daughter

What keeps this music buoyant, even at its bleakest, is the dense triumphalism of the production and the audible rapport between Riley and Pam the Funkstress, his invaluable foil for 20-odd years, whether she was dropping Beavis & Butt-Head grunts into a song called “20,000 Gun Salute” or wowing live audiences with, yes, her famous breast-scratching routine. Revisiting the record now, her heavy presence on Steal This Album adds yet another layer of mournful catharsis: Born Pam Warren, she died in December 2017, at 51, of organ failure. (Shortly before her death, she was pulling double duty as Purple Pam, a.k.a. Prince’s personal DJ.) Per the end credits, Sorry to Bother You is dedicated to both Pam and Riley’s mother, Anitra Patterson.

The Coup’s future is unknown, though an expanded, live-instrumentation-oriented version of the group, joined by luminaries from Killer Mike to E-40 to Janelle Monáe, appeared on July’s Sorry to Bother You: The Soundtrack. But the Pam-Boots alliance will likely never be topped, nor will Steal This Album’s sobering highlight and arguably the duo’s greatest song overall. “Me and Jesus the Pimp in a ’79 Granada Last Night” is a harrowing seven-minute tale of prostitution, revenge, motherly love, and the endless cycle of misogyny that is more complex, and thoughtful, and upsetting, and emotionally resonant than most two-hour movies. Come to think of it, Riley could direct the film version himself. The capitalist system still has its uses.