Michael Penn (born August 1, 1958, in Greenwich Village, New York City) is an American singer and songwriter. He is the son of actor/director Leo Penn and actress Eileen Ryan, and the brother of actors Sean Penn and the late Chris Penn.

Prior to the release of his 1989 debut album March, Penn performed the song "This & That" with his band The Pull on a 1987 episode of Saturday Night Live. Before that, he was a member of the Los Angeles band Doll Congress and had appeared as an extra on a few television series, including St. Elsewhere.

March, particularly the first single, "No Myth," brought Penn attention, as well as the 1990 MTV Video Music Award for Best New Artist. 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." [1]

Penn's music "Walter Reed" was used in the fifth episode of House MD's third season, "Fools For Love".