Handsome Boy Modeling School was 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. The Rockwell name in reference to a pseudonym used by a porn star in 1997 film Boogie Nights
; the Merriweather name is likely an homage to the character "Nathanial Mayweather" also played by Chris Elliott in the 1994 cult comedy Cabin Boy
. A number of guest musicians appear, including Róisín Murphy (one half of the duo Moloko at the time of the album's release), 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 of De La Soul and Del tha Funkee Homosapien was featured in the 2001 film Ocean's Eleven
.Their second album, White People
was released in November 2004. Some collaborators from the first album returned, and new collaborators included RZA, Cat Power, Casual, Alex Kapranos of Franz Ferdinand, Chester Bennington and Mike Shinoda of Linkin Park, Jack Johnson, Cedric Bixler-Zavala of The Mars Volta, Mike Patton, El-P, Pharrell, John Oates, Chino Moreno, Lord Finesse, Black Sheep, and comedy actor Tim Meadows.In 2006, Prince Paul announced his retirement from Handsome Boy Modeling School due to business conflicts with Dan the Automator.