Handsome Boy Modeling School: How A Joke Created One Of Hip-Hop’s Coolest Collabs

Prince Paul lives life as handsomely as possible. Look no further for proof of this than the cover of So... How's Your Girl? the album debut from Handsome Boy Modeling School, on which both he and his co-producer Dan The Automator lounge in their suits, wielding cigars and martinis. Released almost 20 years ago, the record is billed as a musical curriculum, a discounted glimpse into what your enrollment in their college of fashionable cool can get you.

Even before Handsome Boy Modeling School, coolness was something that came naturally to Prince Paul. Though he had co-founded the Brooklyn hip-hop group Stetsasonic earlier that decade, the artist born Paul Huston first came to prominence beginning in the late 1980s by producing for other artists. In 1989, he worked on tracks for 3rd Bass’ The Cactus Album and De La Soul’s 3 Feet High and Rising, each one well reviewed and commercially successful. He would continue to produce for the latter group through 1993’s Buhloone Mindstate. Additionally, he and his Stetsasonic cohort Frukwan formed horrorcore outfit Gravediggaz with Tommy Boy familiar Too Poetic and the Wu-Tang Clan’s RZA, their 6 Feet Deep from 1994 is a celebrated conceptual rap classic.

Despite that impressive run, one which would firmly establish Prince Paul as one of the genre’s golden age greats, the next few years proved difficult for him. “It was tough,” he says. “De La had moved on and so I wasn’t involved in that.” A deal signed with Def Jam to curate and run his own vanity imprint, the boldly named Dew Doo Man label, failed to get off the ground amid changes at, and differences of opinion with, the parent company. Furthermore, after his split with De La Soul, he wasn’t getting the same sort of credits as he’d previously landed. He produced part of Chris Rock’s Roll With The New, a 1997 comedy album that integrated parts of the Saturday Night Live alum’s HBO special Bring The Pain with new sketches like “Champagne,” a Bad Boy Records musical parody. “Thank God Chris Rock came along,” Prince Paul says. (In 2006, he would win a Grammy for his work on the comic’s Never Scared.)

6 Feet Deep, which would eventually go on to become a cultish touchpoint and held in high regard, was nonetheless born out of this challenging period. “The Gravediggaz record didn’t do as good as I thought it would have,” he says. A sophomore full-length called The Pick, The Sickle And The Shovel arrived in 1997, to less fanfare and a greater Wu presence. Notably, Prince Paul had a diminished role in its making, his character the Undertaker largely absent from the production credits and replaced by RZA affiliates like 4th Disciple and True Master.

“I had to take advantage of every opportunity, because I didn’t know if I’d ever make another record again,” Prince Paul says of the period. “I thought my career was over.”

Fortunately, linking with Dan The Automator would prove the spark to reignite his engine both creatively and commercially. “I’d known of Dan for quite some time,” he says. “The handsome circles are very small.” In 1996, Nakamura had played a pivotal role alongside KutMasta Kurt and DJ Q-Bert in shaping the sound of Dr. Octagonecologyst, Kool Keith’s pseudonymous first album following his Ultramagnetic MCs’ farewell bow The Four Horsemen about two years earlier. The album dropped roughly a month or so ahead of Prince Paul’s solo endeavor Psychoanalysis: What Is It? released via underrated indie WordSound Recordings. Skiz Fernando, the man behind that record label, arranged for the two to talk. “We got on the phone and we just clicked,” Prince Paul says.

Beyond respective admiration of one another’s work, the two came together via their mutual appreciation for comedian Chris Elliott, a fandom that Nakamura previously alluded to on the Dr. Octagonecologyst deep cut “halfsharkalligatorhalfman,” a winking reference to the 1994 nautical farce Cabin Boy. That shared fanboy love of an absurdist comedy strain led directly to the ethos of their project, named for a fictitious firm introduced on a episode of Elliott’s early 1990s sitcom Get A Life. In it, the overgrown paperboy protagonist briefly and naively enters the exciting world of fashion by enrolling in the Handsome Boy Modeling School. “I don’t know if we’re underdogs, but we have that mentality of being underdogs,” Nakamura says, drawing parallels to Elliot’s character on the show as well as his regular appearances on David Letterman’s late night programs.

“It’s a rare community of people that actually like that show,” Huston laughs. “A lot of what we did was based on our sense of humor and being music geeks.” In fact, their So... How's Your Girl? is so rooted in that dry, leftfield wit that it literally started as a joke.

“I was hanging out at Tommy Boy and I was on the phone talking to Paul,” Nakamura says, recalling the day of the project’s near accidental genesis. An A&R for the record label interrupted to ask what they were discussing, to which Nakamura quipped “Handsome Boy Modeling School,” casually mentioning it was their new group. Of course, it didn’t exist, but that didn’t stop him from talking it up as a sort of “hip-hop Chemical Brothers.” Tommy Boy had already made a name for itself in rap, though at that time it was also home to dance music sensation Amber and former House Of Pain rapper turned alternative folk singer Everlast. Even without hearing a single note, as no such note had been recorded, label president Monica Lynch immediately saw the potential and signed the duo. “It seemed like the universe just put everything in line for us to make this record,” Huston says.

A remix of the Dr. Octagon cut “Blue Flowers” technically marked the pair’s first shared credit, yet their common interests had already set into motion a more properly collaborative union. With Nakamura more of a gearhead than the self-admittedly less technologically inclined Prince Paul, the two might not seem ideal partners on paper. In practice, however, they were kindred spirits who turned their madcap vision and eclectic tastes into something idiosyncratically singular. Donning the Handsome Boy Modeling School monikers Nathaniel Merriweather and Chest Rockwell, they challenged one another to operate in a manner more like the other without any pressure to sacrifice on individuality.

“We were just going to find music that was the soundtrack to our daily lives of being handsome men,” Huston says, launching into a mock dialogue that encapsulates the nature of their partnership. “Does this makes you feel handsome? No. How about this? Oh, that’s very handsome.”

Being open-minded producers with authentic connections to a variety of artists, their respective rolodexes got one hell of a rolling through in the making of So... How's Your Girl?. Prince Paul’s ties to east coast hip-hop led to him calling in favors from Brand Nubian members Grand Puba and Sadat X, WordSound signee Sensational, and Company Flow’s El-P, among others. Nakamura, in turn, brought in the likes of Del The Funky Homosapien and Kid Koala, who he’d reteam with soon thereafter as the sci-fi trio Deltron 3030. With collaborators as disparate as Beastie Boys rapper Mike D, digital hardcore don Alec Empire, and members of Cibo Matto, the album makes for a unique listening experience, frequently funny and always inventive, taking its seemingly hodgepodge genre twists to interesting and even exhilarating places.

“We both, individually and collectively, attract certain kinds of people,” Nakamura says, referring to the guests as personal friends. “Once we started making the album, we were filling in the blanks.” To manage the sheer number of participants, Huston says many of their performances were recorded outside the studio environment, sometimes with portable equipment in less than conventional settings. “A lot of it was kamikaze,” he stresses.

One of the record’s most surprising features comes from Father Guido Sarducci, a character played by SNL writer Don Novello who frequently appeared on the show in the 1970s. During the making of So... How's Your Girl? a friend of Nakamura’s had invited him out for dinner, only to find that he had brought along the actor as well. Unwilling to sacrifice the opportunity, he explained the project and asked if he would participate. “I think he went to the studio that night,” he says. The resulting skits play into the Handsome Boy Modeling School mythos, with Novello hilariously espousing the virtues of the institution under the guise of his chain-smoking Catholic priest. “Father Guido Sarducci is real handsome,” Huston says. “And he has a mustache!”

Handsome Boy Modeling School would go on to release a follow-up to So... How's Your Girl? five years later, the provocatively titled White People. As with the prior installment, it continued their mission with a similarly wide-ranging set of guests, including David Lynch chanteuse Julee Cruise, SNL veteran Tim Meadows, and Oates of Hall & Oates. In between the two albums, Nakamura repurposed his Nathaniel Merriweather moniker for use in Lovage, a downtempo group with Jennifer Charles of Elysian Fields and Mike Patton of Faith No More. With respect paid to Serge Gainsbourg upfront, their 2001 full-length Music To Make Love To Your Old Lady By opens with an appearance by none other than Chest Rockwell himself.

To some extent, Handsome Boy Modeling School’s legacy may very well be its prescience of the image-obsessed social media world that was then soon to come. Today’s lifestyle landscape has millions of people following every Kardashian Twitter moment or Instagram story, with countless others fancying themselves influencers or online personalities in the service of individual vanity and a superficial aspirational desire toward recognition. Though fully aware of where things were going culturally, Huston regrets not foreseeing how technology would prove this out. “We would’ve invested in Instagram back then, made apps and sold them!”

Even as the duo coyly hint at the possibility of a third album sometime in the future, Nakamura sees the work that he and Huston accomplished on So... How's Your Girl? as helping set at least one major trend in the music that followed. “Think about it: when that record came out, was there ever a record like that,” he asks rhetorically. “If you take the two Handsome Boy records and put them together, they’re pretty much the roadmap for modern pop collaborations.”

Eternally fixated, Huston prefers to see their foresight via a sartorial lens. “We were wearing Euro fitted suits back in the ’90s, when everybody else was wearing baggy clothes,” he says. “Now everybody’s wearing fitted suits!”

“That’s why we’re thinking of bringing the school back. People gotta get back to the basics of handsomeness.”