In the late 1990s, Hip-Hop was taking itself a bit too seriously—at least in the eyes of two highly-accomplished producers. An era remembered for its high-profile beefs, Champagne-poppin’, and colorful and shiny videos was rich fodder for some veterans who wanted to jerk the steering wheel with creativity in mind.

Great satirists, producers, and DJs, Prince Paul and Dan The Automator, mocked society’s uber-elite in 1999 as a duo with their concept album dubbed as “The Music Curriculum Of Handsome Boy Modeling School.” The LP was whimsically-titled So…How’s Your Girl?, evoking the narcissism and materialism of celebrity culture and wealthy one-percenters. The cross-country pairing of Dan and Paul was a fitting match coming off the heels of their respective critically-acclaimed concept albums, Dr. Octagonecologyst (with Kool Keith and DJ QBert) and the first “Hip-Hopera” ever recorded A Prince Among Thieves. Paul had always been a proud detractor to Rap music industry conventionalism with his seminal role in De La Soul’s first three albums, “horror-core” brainchild Gravegdiggaz, and his self-proclaimed “middle finger to everybody,” Psychoanalysis (What Is It?). 

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The Handsome Boy Modeling School took some of its posture from “The Prettiest Week Of My Life” episode of Chris Elliott’s early ’90s FOX TV show, Get A Life. In that ep’, the show’s main character (“Chris Peterson”) enrolls in the school. Throughout the album, Elliott’s excerpts are used. Notably, Elliott also played “Nathaniel Mayweather” in the 1995 film Cabin Boy, from which Dan The Automator made a variation of the name “Nathaniel Merriweather” for the album. Paul adopted his “Chest Rockwell” moniker from John C. Reilly’s porn stage name in 1997’s Oscar-nominated Boogie Nights. 

As the ultimate set-up for the album, Paul, Dan and Tommy Boy Records made a promotional infomercial for the school. Made years before such promotional content was widely available online, the five-and-a-half minute spot shows the school teaching some poses. With N*SYNC, Scarface, and James Dean posters in the classroom, a group that includes El-P (in a Non-Phixion tee) and Rahzel learns just what it takes. Don Novello, who played his Saturday Night Live character of “Father Guido Sarducci,” reprises the role for a “class of ’88” success testimonial. Meanwhile, “Chest” and “Nathaniel” smoke cigars, asking only two easy payments of $30 to admit. Fictional number 212-338-U-DOLL dominates the screen, beckoning your business:

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The resulting Tommy Boy/Warner Bros. album defied genre. It was filled with guest appearances from some of Hip-Hop’s brightest, including Beastie Boys’ Mike D, De La Soul’s Dave, Del The Funky Homosapien, Brand Nubian’s Sadat X and Grand Puba, Biz Markie, El-P, Encore, J-Live, turntablist, Kid Koala. Songstress Róisín Murphy, DJ Shadow, and Sean Lennon also rounded out the guest-list. “Father Guido Sarducci” was a role-player to the album’s comedic undertone.

Every track on the album takes the album in a new direction but in a cohesive fashion. The standout tracks that proved the album’s wide range of sounds from the album were Del’s performance on “Magnetizing” and “The Projects (PJays)” with Dave. The ghostly “Waterworld” featuring Cali rapper Encore, the campy “Metaphysical” featuring Mike D and Miho Hatori of Japanese female Rap duo Cibo Matto, and an ethereal serenade by Róisín Murphy with a muscular rap verse from MC/DJ J-Live on “The Truth.” The arguably best track on the album was DJ Shadow’s “Holy Calamity (Bear Witness II),” a reprisal of an Octagon cut. 

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Paul went on to release additional solo material, in addition to co-founding BROOKZILL! and Baby Elephant. Dan dropped solo materials and co-founded Deltron 3030 in addition to acclaimed work with The Gorillaz. In 2004, Dan and Paul released their Handsome Boy follow-up, White People. Earlier this year in February, Dan and Paul announced their reunion for a new Handsome Boy Modeling School for 2019, which will be the 20th anniversary of the School’s opening.

Additional Reporting by Jake Paine.