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 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...