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Look at These Faces: How Handsome Boy Modeling School Created the Perfect Album for ’99

Producers Prince Paul and Dan the Automator invited all of their good-looking friends to a party 20 years ago, and the result was a weird, hilarious rap record that stands the test of time

Getty Images/Ringer illustration

Welcome to 1999 Music Week, a celebration of one of the most interesting, vivid, varied music years ever. Join us as we count down the best singles and albums of the year, remember the days of scrubs and the girls who wear Abercrombie & Fitch, and argue about which albums stood above the rest.

“You ever see that ’60s television show Batman?” Daniel Nakamura, a.k.a. outré polymath producer Dan the Automator, a.k.a. one-half of the spectacular underground-rap duo Handsome Boy Modeling School, a.k.a. his HBMS playboy alter ego Nathaniel Merriweather, was joking. Probably. He was explaining, in as irreverent a manner as possible, how the group goes about selecting its sublimely motley crew of collaborators. “Crime happens in the city and the commissioner throws up the bat signal and all of a sudden Batman shows up, jumping through the window? It’s kind of like that,” this explanation continues. “The Handsome Signal goes up, and the handsome people come around.”

Nakamura and his crime-fighting associate Paul Edward Huston, aka outré polymath producer Prince Paul, a.k.a. his HBMS playboy alter ego Chest Rockwell, were chatting with The Guardian in 2004 on the festive occasion of the duo’s absurdly star-studded second album, White People. Great record. (The guest stars, a.k.a. this particular round of Handsome People, include Pharrell, the RZA, Cat Power, Tim Meadows, Jack Johnson, and John Oates from Hall & Oates.) Incredible cover. Spectacular title. White People is, in fact, nearly as good a record (and title) (and cover) as Handsome Boy Modeling School’s sterling debut, So … How’s Your Girl?, which I will hereby argue is the best album, in any genre, of 1999.

I’m not joking. Incredible cover, for starters. (We can certainly agree, with apologies to Quentin Tarantino, that So … How’s Your Girl is the best use of a title ellipsis in any medium, anytime.) It is easier perhaps to argue that this is the most 1999 rap album of 1999, a playful and eccentric kitchen-sink symphony full of transcendent sample-based silliness and whimsically cerebral rapping emblematic of an underground scene getting weirder and wilder, atomizing and metastasizing at a fearsome rate, inching closer to pop music’s center even as its freak flag flew ever higher. Let’s fix Jay-Z’s Vol. 3... Life and Times of S. Carter (poor use of an ellipsis, though) and Eminem’s The Slim Shady LP as that year’s mainstream pinnacle, with the Roots’ Things Fall Apart and Mos Def’s Black on Both Sides among the thinking rap fan’s theoretically classier alternatives. And let’s celebrate So … How’s Your Girl as too defiant for the big time and too defiantly goofy to settle for ruling the underground, either.

That’s all true. But it’s preferable that one’s relationship with a record this singularly itself be personal, and moreover be as random and unserious as possible, which is why the first thing I want you to know about So … How’s Your Girl is that back in 1999 I used to terrorize my fellow DJs at our Midwestern college-radio station by blasting the exuberant turntablist workout “Holy Calamity [Bear Witness II]” at incredible volume. Your Handsome People at this juncture are DJ Quest and the mighty DJ Shadow, he of 1996’s epochal sampling collage Endtroducing…..; the result is more pure absurdist joy than one four-minute track can ordinarily stand. (Shout-out Entroducing….., featuring the ultrarare acceptable five-dot ellipsis.) I want you to imagine this righteous jam disrupting stately blocks of indie-rock-ish tunes from Built to Spill, the Flaming Lips, Wilco, and so forth. I want you to imagine my delight as a method of preparing to be overwhelmed by your own.

You ever see that ’90s television show Get a Life? No. Of course you haven’t. Don’t worry about it. Starring the supremely polarizing Chris Elliott, an acquired taste too cringey and confrontational even for many proponents of the era’s thriving alt-comic scene—shout-out 1994’s Cabin Boy, the best terrible movie ever made—it lasted two low-rated seasons on Fox, from 1990 to 1992. Elliott plays a grating 30-year-old man-child still living with his parents; in the second-ever episode, he decides to become a male model and enrolls at the Handsome Boy Modeling School behind a carpet warehouse. Tuition is $60. Things go poorly: Elliott soon finds himself him shirtless and humiliated. “Modeling just sucks,” he concludes. I bet you’re wondering how that phrase would sound paired with boom-bap drums and the opening riff from Beethoven’s Fifth Symphony. I laugh out loud at this, every time.

And just like that, the rap duo Handsome Boy Modeling School had a name, and a concept, and an ethos, and a bevy of pathetic Elliott-based samples from which to draw. East Coast legend Prince Paul is best known for his wily and fearless production work on the first three De La Soul records, perfecting the very notion of a rap-album skit on the trio’s 1989 debut 3 Feet High and Rising. He’s an irreverent guy, though he takes that irreverence dead-seriously: Paul’s first solo album, from 1996, was called Psychoanalysis: What Is It?!, while the follow-up, February 1999’s A Prince Among Thieves, is a long and knotty and legitimately cinematic behemoth that might be as close as rap music ever got to an honest-to-god rock opera.

West Coast legend Dan the Automator, meanwhile, was back then best known for his wily and fearless production work on Kool Keith’s 1996 oddball opus Dr. Octagonecologyst, among the most beloved truly weird rap albums ever born. (He worked on DJ Shadow’s Entroducing….., in fact; just a little more recently, he made his feature-film debut with the score to Booksmart.) In 2001, he joined the crew behind Blur frontman Damon Albarn’s self-titled debut album as Gorillaz, leavening, along with comics whiz Jamie Hewlett, Albarn’s fundamental pompousness. From a 2001 Spin profile of Gorillaz:

Back in Hewlett’s hotel room, as everyone enthusiastically guzzles record-company champagne, Albarn describes his search for an alternative to Britpop’s creative dead end.

“Three years ago, I sat down with Can in Cologne—”

“Whoa!” Nakamura interrupts, his mouth stuffed with jelly beans. “How pretentious is that? I sat down with Can in Cologne.”

I have associated Nakamura with the phrase his mouth stuffed with jelly beans for the past 18 years. God bless him. Handsome Boy Modeling School is best thought of as a lighter, looser, funnier, and all-around better (not to mention earlier) version of the Gorillaz approach, high-concept but deliciously lowbrow, down to hang out with anyone without disrupting the album’s expert cohesion. Early on, So … How’s Your Girl, released in October ’99, features back-to-back rap showcases from Bay Area titan Del Tha Funky Homosapien (his cocky and loopy delivery of the words full color high-res has likewise stuck with me for 20 years) and Miho Hatori, she of beloved NYC-via-Tokyo art-pop duo Cibo Matto. (Ditto for the way she raps Reflective imagery burned into the cornea of interdimensional transglobal marketing schemes as the Beastie Boys’ Mike D mumbles in the background.)

This is a very strange but wildly appealing album, full of 1999-vintage lyrically lyrical “got your third eye crying”–type rapping (that’s from Del) bolstered by Dan’s and Paul’s god-level skill at both conceptual scaffolding (the skits are great, including the one where Biz Markie sings the Bee Gees) and crate-digging. Brand Nubian rappers Grand Puba and Sadat X drop by; so does fellow turntablist wunderkind Kid Koala. The worst track, which is called “Megaton B-Boy 2000,” features future Run the Jewels luminary EL-P howling over an industrial freakout from Alec Empire, he of German noise-rockers Atari Teenage Riot. The best track, which is called “The Truth,” masterfully flips a dusty soul-funk jam from Hair composer Galt MacDermot and features both NYC rapper J-Live and Irish trip-hop torch singer Róisín Murphy.

None of this should work, or certainly none of this should work together. The other track I used to blast at incredible volume on college radio, when I was done terrorizing people, was a slinky R&B slow jam called “Sunshine,” crooned immaculately by Sean Ono Lennon, Beastie Boys cohort Money Mark, jazz scion and slowcore innovator Josh Haden, and former Faith No More singer Paula Frazer. Oh, plus jovial spoken-word interjections from ’70s Saturday Night Live star Father Guido Sarducci, who provides the album’s, uh, closing prayer. Somehow all these people sound as natural together as the Beatles.

Given his celebrated association with the star-crossed De La Soul, it would not be a Prince Paul project, unfortunately, without sampling issues or other music-biz calamity screwing up this album on streaming services. The Spotify version of So … How’s Your Girl replaces the original “Sunshine” with an eight-minute “Sunset Dub” courtesy of the English electronica duo Groove Armada. Too bad. But consider that just one more strong flavor for the album to absorb without diluting that flavor one iota. White People was, alas, the last Handsome Boy Modeling School album to date, though in late 2018 Prince Paul tweeted that a new record is forthcoming. Don’t bet the farm on that, maybe. But if it does come to pass, expect a daffy and incongruous guest list that coheres, however improbably, into the most logical and delightful house party two ’90s rap giants could ever hope to throw, jelly beans stuffed in their mouths. No matter the era, no matter how unlikely the circumstances, when the Handsome Signal goes up, the handsome people come around.