Handsome Boy Modeling School was a hip hop collaboration between Dan the Automator and Prince Paul, producer of rap trio De La Soul. Handsome Boy Modeling School is a conceptual hip hop duo that parodied and acted as a commentary on vain, consumerist, materialistic, and self-absorbed members of upper class society, such as supermodels and people from old money.
The pair often satirized upper class snobbery and perceived beauty.
In 1999, they released the concept album So... How's Your Girl?, which was loosely based on an episode of the Chris Elliott sitcom Get a Life entitled "The Prettiest Week of My Life." The episode also contains the origin of the name Handsome Boy Modeling School, where Chris Elliott's character enrolls to become a male model. In the album, Dan and Paul assume the characters of Nathaniel Merriweather and Chest Rockwell, respectively. A number of guest musicians appear, including Del tha Funkee Homosapien, J-Live, Sean Lennon, Miho Hatori (of Cibo Matto), Mike D (of the Beastie Boys) and Don Novello (as comic character Father Guido Sarducci).
Their 1999 single "The Projects" in collaboration with Trugoy, De La Soul and Del tha Funkee Homosapien was featured in the 2001 film Ocean's Eleven.
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