Penn's follow-up albums Free-for-All (1992), Resigned (1997) and MP4: Days Since a Lost Time Accident (2000) weren't able to match the success of March, although critics praised his songcraft. Penn met fellow singer-songwriter Aimee Mann in the late 1980s, and during the recording of her album I'm With Stupid (to which Penn contributed vocals), the two struck up a friendship, which blossomed into romance and their 1997 marriage. Together with manager Michael Hausman they formed United Musicians, which is based on the idea of allowing artists to keep copyright ownership of their works and to assist with their promotion and distribution. Penn and Mann live in the Los Feliz neighborhood of Los Angeles. They have no children, but Penn has a son from a previous marriage. He moved into film scoring after repeated requests from director Paul Thomas Anderson, who had apparently listened to Free-for-All extensively while writing his first feature Hard Eight and wanted Penn to score the film.
Penn also scored Anderson's follow-up Boogie Nights (in which he appeared briefly as a recording engineer), The Anniversary Party, Melvin Goes to Dinner and the documentary The Comedians of Comedy. His fifth album, Mr. Hollywood Jr., 1947, was released August 2, 2005, on Mimeograph Records (Penn's own label) and SpinART Records. Penn has said that the album, which may be the first of two parts, is set after World War II and involves "the trauma that a war brings to a person's psychology."  Penn's music "Walter Reed" was used in the fifth episode of House MD's third season, "Fools For Love". Read more on Last.fm.
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