During the editing of the film, Anderson directed a music video with Penn for "Try" from "Resigned" (the video can be found on the "Boogie Nights" DVD). Other films scored by Penn include Alan Cumming's first two directorial efforts, "The Anniversary Party" and "Suffering Man's Charity"; "American Teen", "Sunshine Cleaning"; the documentary "The Comedians of Comedy"; and "The Last Kiss". In 2003, he was nominated for a DVDX Award for Best Original Score in a DVD Premiere Movie for "Melvin Goes to Dinner". Penn has produced recordings for Aimee Mann, The Wallflowers and Liz Phair. In August 2005, Penn released "Mr. Hollywood Jr., 1947" on his own Mimeograph Records label. Its songs are set against the background of post-World War II Los Angeles; Penn said he chose the year because of several notable events that took place then, including the passage of the National Security Act and the invention of the transistor. The album was reissued by Legacy Recordings in April 2007 with bonus tracks from a KCRW session. The reissue came in conjunction with Legacy's release of "Palms and Runes, Tarot and Tea: A Michael Penn Collection", a compilation that includes several alternate versions and previously unreleased songs. Penn said his goal in compiling, ordering tracks for and producing "Palms and Runes" was to "make it feel like an album" in its own right. In late 2009, Penn composed the music for the film "That Evening Sun". In 2012 Penn began work as the composer for the HBO TV show "Girls". In January 2013, the "Girls VOL.1" soundtrack was released on iTunes. The album contained a new song by Michael Penn titled "On Your Way", which was featured in the finale of Season 1. He also joined the crew of Showtime's "Masters of Sex" in 2013 as series composer. The show's pilot episode was initially set to be scored by Thomas Newman, but this did not come to fruition and Penn scored both the pilot and the rest of the series. In 2018, he joined two new TV series as a composer - "Good Girls" on NBC and "Here and Now" on HBO. Penn met fellow singer-songwriter Aimee Mann, and during the recording of her album "I'm with Stupid" (to which Penn contributed), the two struck up a friendship, which blossomed into romance and their December 29, 1997 marriage.