[1] Prior to the release of his 1989 debut album March, Penn was a member of the Los Angeles band Doll Congress.

Penn was one of two musical guests as a solo artist on Saturday Night Live on the October 24, 1987 episode, with his brother Sean hosting.

Penn's follow-up albums Free-for-All (1992), Resigned (1997), MP4: Days Since a Lost Time Accident (2000), Mr. Hollywood Jr., 1947 (2005) and Palms and Runes, Tarot and Tea (2007) weren't able to match the commercial success of March, although critics continued to praise his songcraft.

[3] Penn collaborated with surrealist animators The Brothers Quay on "Long Way Down (Look What the Cat Drug In)", which was shown on MTV as well as in film festivals around the country.

He scored Paul Thomas Anderson's films Hard Eight (1996) and Boogie Nights (1997); he also appears in the latter in a cameo role as a recording engineer.

Other films scored by Penn include Alan Cumming's first two directorial efforts, The Anniversary Party and Suffering Man's Charity;[4] American Teen, Sunshine Cleaning;[5] the documentary The Comedians of Comedy; and The Last Kiss.

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.

[8] 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.