Handsome Boy Modeling School is a hip-hop collaboration between Dan the Automator and Prince Paul, producer of influential rap trio De La Soul. 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 Chester Rockwell, respectively. A number of guest musicians appear, including Del tha Funkee Homosapien, J-Live, Sean Lennon, Miho Hatori (of Cibo Matto), Grand Puba, Sadat X, Biz Markie, Mike D, and El-P.
