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The world of music has moved on greatly from 1999, the year that Prince Paul and Dan the Automator got together and released the first of two Handsome Boy Modeling School albums, So...How's Your Girl. Three years previously, DJ Shadow, who would be one of the contributors to that album, got in the Guinness Book of World Records for releasing the world's first album made solely by sampling. At the time, "electronic music" was still seen as a possible fad, a brief experimental blip following the resurgence of guitar driven alternative rock bands. Many of the innovations of this era would become the mainstream way that music was produced, but at the time, this album was a novelty.

I came back to Handsome Boy Modeling School, listening to the two albums after years of separation. I can say that in most ways, the idea and execution of the albums has held up very well.

Handsome Boy Modeling School was a supergroup of obscure figures, releasing concept albums without any concept behind them. On paper, hearing a description of the tracks, it almost seems like an elaborate prank and joke. Which it was, but it also featured some heartfelt, skillful, and innovative songwriting and production. After two decades, I still don't know what to make of this, which is perhaps the point.

A bit of background: "Handsome Boy Modeling School" was the brainchild of Prince Paul, a well-connected New York City DJ and producer, whose previous single greatest claim to fame was producing De La Soul's psychedelic tinged first album, Three Feet High and Rising. Dan the Automator, from the San Francisco Bay area, had one major achievement, producing Dr. Octogonecologyst. They met and, together with a very random assortment of friends and friend's friends from the music industry, started recording music in a variety of styles. Connected with clips from a single episode of the comedy show Get a Life. At base, this is was a hip-hop album, and at least one track, featuring Brand Nubian, was an old school, street corner dis track. But most of the album weaves around different hip-hop style. One song, Metaphysical has Miho Hatori from Cibo Matto speaking tonelessly over an electronic background. But to explain the album best, I would use "Sunshine", a song featuring Sean Lennon and Josh Haden singing a soft, jazzy duet. Interspersed with a comedic monologue by Don Novello as Father Guido Sarducci. It is hard to understand the process that led from a hip-hop album to soulful jazz sung with comedy interludes...and the A&R department that let this all happen.

The second album, "White People" was released in 2004, when much of the 90's enthusiasm for DJing and producing had waned, and when the world itself had moved on to a different era. The album was even more experimental in its choices, and sometimes the collaborations seemed to be chosen by drawing names out of a hat. Do you want to hear 90s rockers Linkin Park with hip-hop pioneer DJ Jazzy Jay? Do you want to hear alternative rock band Mars Volta with the RZA from The Wu-Tang Clan? Actually, you do, even if you don't know it. Although how this relates to Mike Patton from Faith No More and soul singer Cat Power is not exactly clear. And when we finally reach John Oates and Jamie Cullum singing what sounds like easy listening, I do wonder how exactly we got from experimental, hardcore hip-hop to this.

In some ways, the precedent I could best use to explain what Handsome Boy Modeling School was meant to be would be to evoke The Beatles' White Album. The White Album also feels like a concept album, despite having no single voice or theme to unify it. And like the White Album, it varies from avant-garde sonic experimentation to songs that are designed to be catchy. And even when it is parodic, it is earnest. Like the White Album, Handsome Boy Modeling School doesn't seem to have a single ideological viewpoint to pursue, but it is clearly a product of its time, with many topical allusions. This might seem like a rough comparison, but this is the best way I can explain why the two Handsome Boy Modeling School albums still appeal to me, almost two decades after their release.