Prince Paul is responsible for some of the most important music in the hip-hop canon, but despite his contributions, he is also hip-hop’s perennial odd man out. Too often overlooked, sometimes rejected, and at various points dispossessed by the music biz, Paul Huston’s alternating perspectives as insider and outsider have given him a unique ability to engage with the absurdity of it all. A Prince Among Thieves, is, on its surface, a masterpiece of humorous hip-hop storytelling over 35 tracks and 77 minutes, featuring an ensemble cast of Golden Era rap stars and underground legends. What lies beneath, however, is biting satire born of a decade of career hardships and their residual effects on the psyche of this goofy genius from Long Island.

In the 1980s, Prince Paul was a bright-eyed, prodigious teenager who earned a rep in the black suburban enclave of Amityville, New York as a young DJ with skills and taste. His rep would stretch to the streets of East New York, Brooklyn, where lauded hip-hop band Stetsasonic added him to the group, first as their DJ and later as one of their in-house producers. Seeking more autonomy to execute his left-field ideas, Paul connected with three like-minded young men who attended his alma mater, Amityville Memorial High School. In De La Soul’s Posdnuos, Trugoy, and Mase he found kindred spirits who were just as nerdy and willing to get weird as he was.

With his new creative accomplices, Paul sought to upend the rap clichés of the day. While other hip-hop producers were wringing James Brown’s catalog dry of samples, Paul and De La’s eclectic palette of sources included everything from Johnny Cash to Sly and the Family Stone. Where their contemporaries wore gold, De La wore black leather Africa medallions; where their peers were self-important, they were at times self-effacing; and while other acts were busy coming out hard; De La came with jokes.

Their formula worked. 1989’s 3 Feet High and Rising gained widespread critical acclaim, as did De La’s 1991 sophomore effort, De La Soul Is Dead. Together, the four young men subverted stereotypes, expanded rap’s sample palette and perfected the rap album skit as a storytelling device, making them essential to the cohesion of an album. Riding high off of these successes, Prince Paul was, for a few years, an in-demand producer working with rap’s hottest acts at the time, including Big Daddy Kane, Slick Rick, Queen Latifah, Boogie Down Productions, and 3rd Bass—he even produced a song for Brooklyn MC the Jaz on which a young JAY-Z rapped and shouted him out by name.

The remainder of the ’90s weren’t as kind to Paul. These days, it’s entirely possible for rappers like Drake or producers like Pharrell to enjoy years-long hot streaks In hip-hop’s adolescence, rappers were lucky if they made it to a third album without getting dropped by a label, and producers may have had a window of a year or two while their sound was hot before the music of the day moved past them. To an early ’90s audience that was increasingly becoming enamored with the sounds of gangsta rap coming from the West Coast, Paul’s signature weirdness and eclecticism were passé. Paul and De La found also found themselves growing apart creatively during the making of the group’s third album, Buhloone Mindstate. Suddenly, the guy who co-produced the answering machine jam “Ring Ring Ring (Ha Ha Hey)” couldn’t get his hip-hop friends and associates to return his calls.

By the middle of the decade, Paul’s career was in decline and his personal life was in disarray. His imprint Dew Doo Man Records had failed, he was De La Soul-less, and on top of it all, he was embroiled in a custody battle with his ex-girlfriend over his son, Paul Jr. Paul prepared to say goodbye to the music biz with a final middle finger in the form of his 1996 album, Psychoanalysis: What Is It?!. The record was an equally bizarre and intriguing exploration of the recesses of his mind, featuring his far-from-famous, ’round-the-way friends on vocals. His taste for absurdity was now tinged with disillusionment and his humor was at it darkest. Paul explained the thinking behind the project in an appearance on The Cipher podcast in 2015: “My career’s over, people hate me, nobody’s gonna hear this record ... Let’s make this record all about somebody who has all these psychoses and all this other crazy stuff and not worry about what people will say.”

To his surprise, the album earned acclaim as an oddity on the hip-hop spectrum and soon, his former label Tommy Boy reached out to re-release the album and to work with him again. Tommy Boy wanted Paul to be their resident prestige artist at a time when they were making money from pop-rap acts like Coolio and Naughty By Nature. Reinvigorated by the new interest, he pitched an idea: Instead of an album with a narrative told solely through skits, why not do an album that’s a story from beginning to end? The project could be acted out through low-budget music videos, and the label could launch Tommy Boy Films with it. The label bit on the idea of the album but tightened their purse strings when it came to film production costs. In those days, digital video wasn’t readily accessible, and proper filmmaking was too expensive. They put up a measly $10,000 for him to shoot a trailer.

Undeterred and even inspired, Paul wanted to create something at the intersection of schlock and hip-hop—funny, off-kilter, and entertaining. “I wanted to make a movie on wax, I wanted to make an adults’ kid album,” he told Complex in 2011. As he started to piece together the plot of the album, he studied the B-movies he loved growing up, adapting the most cliche scenes for his script. Deciding how he would end this story, Paul thought about the bumps and bruises he had acquired in the years prior and indulged the chip on his shoulder. Thinking back to all of his disappointments and failures in the music biz, and a family court proceeding where a judge awarded his ex-girlfriend custody of their son, the idea that would underpin the story came to him: “The bad guy always wins.”

The story would center on a schmuck of a protagonist named “Tariq,” an aspiring rapper and part-time slacker in need of $1,000 to finish recording a demo for an impending meeting with the RZA. To get the money in a week’s time, he reaches out to his not-nearly-as-straight-laced friend, True, who, instead of loaning him the cash, offers him entrée into the criminal underworld to earn it. A naive and gullible Tariq would quickly learn that a grand don’t come for free and fall victim to dirty-dealing and betrayal. Tariq was a victim of shady people, circumstance, and poor decisions. Tariq was Paul.

With the tragicomic storyline sorted out, Paul had to play casting director, too. Though Psychoanalysis re-opened the door to work with people like comedian Chris Rock, it did not fully restore the industry clout he had enjoyed in his heyday. Tommy Boy wasn’t giving him a huge budget, so ideas like getting Notorious B.I.G. to play “True” were out of the question. So he would do what he had always done—appeal to the outcasts.

For his cast of rappers-turned-voice actors, he sought out underground emcees to play the main characters and rappers who had been largely deemed over-the-hill as the supporting cast. For the lead, he tracked down Breeze Brewin of the underground rap group the Juggaknots. In the mid-’90s, Breeze Brewin went from being doomed to obscurity after his group was dropped from East West Records to being a part of the vanguard of a burgeoning college radio-propelled NYC underground rap micro-scene that included El-P and his group Company Flow as well as acts like Non-Phixion and Natural Elements. Prince Paul knew Breeze Brewin’s serpentine flow—full of internal rhyme schemes and tongue-in-cheek jokes—would be perfect for A Prince Among Thieves; a starstruck Breeze Brewin jumped at the chance to work with a man he considered to be a living legend.

For True, Paul cast a rapper named Sha from a local Amityville group called Horror City. Paul called in favors to round out the rest of the cast: a post-House of Pain and pre-Whitey Ford Sings the Blues Everlast played the racist crooked cop “Officer O’Malley Bitchkowski”; Kool Keith was “Crazy Lou,” a crazed black-market arms dealer who was an ex-Marine captain “discharged for sexual misconduct with a deadly weapon” (read: he fucked guns); Big Daddy Kane was a smooth-talking pimp named “Count Mackula”; Xzibit, Kid Creole, and Sadat X played rowdy convicts in a jail cell; Breeze’s younger sister, rapper Queen Herawin, played Tariq’s skeptical yet loving girlfriend; and Chubb Rock was the kingpin, “Mr. Large.” Paul’s old crew De La Soul even popped up with Chris Rock to play over-eager crack addicts.

“The crazy thing about making that album is that nobody knew what was going on,” Paul told Shawn Setaro of The Cipher. “Nobody knew the whole story, how it went. I gave people [their] parts and they didn’t see the other person’s part and I just recorded [them] line for line for line and edited it all together.” This was 1998, years before Pro Tools was in wide use, so Paul went about the tedious work of putting together the music piece by piece and the dialogue line by line using an ASR-10, ADAT digital tapes, and a MIDI sequencing program. For the project’s beats, he simplified his approach, making the tracks from a sample or two with overlaid drums programmed onto them. It was more economical and it put the story and his players in the foreground.

After nearly two years of work, A Prince Among Thieves was released in February 1999. The album begins at the end of the story, as EMTs attend to our wounded protagonist. Sirens wail in the background and Tariq’s internal monologue sets the stage. The skit gives way to the mournful strings of “Pain” where we discover that Sha has also been shot. As Tariq, Breeze Brewin paints a picture of violence and betrayal that tease the twists and turns to come. He’s presented as a relatable loser who lives with his mom on “Steady Slobbin.” Flipping the concept behind Ice Cube’s day-in-the-life-of-G “Steady Mobbin,” our protagonist recounts all of the L’s he takes during his day, from being broke and harangued by his mom to his premature ejaculation during in a sexual encounter with an unattractive woman.

To flesh out the characters, Tariq gives us some background on his relationship with his sly-tongued homie True on “Just Another Day”: The two go way back. True taught Tariq how to rhyme when they were younger but wound giving up his rap dreams when Tariq surpassed him. Tariq detects envy but figures something so small could never come between brothers. The contradiction and cognitive dissonance lend depth to the two main characters and their relationship while grounding the cartoonish supporting characters we meet later. Paul’s dim view of human nature at the time informs the story, as Tariq sets out on his Faustian path to $1,000, his morals loosening along the way.

In a genre that was, especially at the time, obsessed with authenticity and realness, Paul delighted in skewering cliches with the sharp tip of satire. Recurring themes in rap that had since become tropes were now fodder for parody, as Tariq made his descent into the underworld. To get a gun—de rigueur for any aspiring hustler or posturing rapper—he has to visit Kool Keith’s “Crazy Lou,” at his hideout (the password is “enema bandit”). The romanticized subject of guns gets sent up as Kool Keith runs down a list of real and fantastical firearms before unveiling his ultimate weapon: a “six-foot gorilla” with “the aluminum skin of an alligator” otherwise known as “Dragon Plus ... with a twist.” By the time he’s done talking about this imaginary arsenal, you’re unsure if the weapon he’s just described is animal or mechanical but you are certain that it is nonsense. You can almost hear Paul giggling in the studio.

And what allegory about temptation would be complete without sex? A hilariously simulated love scene—complete with a boinging sound effect to signify an erection—is interrupted by Everlast as a crooked NYPD officer. The character is another stroke of comedic genius: He embodies every stereotype of a racist New York City cop with lines like, “It’s the Bad Lieutenant runnin’ up in your tenement/Plantin’ evidence on any black resident,” and, “I’ll shoot you in the alley/And burn you like a cross at a fuckin’ Klan rally.” But characters like Everlast’s and Big Daddy Kane’s “Count Macula” are more than just cool cameos in Paul’s cynical story, they are agents of betrayal. Characters meant to convince the listener that the odds are stacked against the good guys. They’re Paul’s adversaries, disappointments, and failures personified.

For all of its surprises, Easter eggs, guest stars, the dramatic center of A Prince Among Thieves remains Breeze Brewin’s Tariq. When he realizes that he’s been set up and the extent of the betrayal our loveable simp is overcome with a vengeance that leads him to a Western-style showdown on “You Got Shot”: “It’s hard to live/Knowin’ that you’re doing the same/Knowin’ ‘bout you and your game/Let God forgive, I won’t...” His innocence lost, Tariq’s climactic transformation from gullible chump to jaded would-be avenger mirrors Paul’s experience in the music biz. But Paul, our auteur, knows that righteousness and victory seldom come together.