Family
- father Leo Penn: Was a drama teacher at the Actor’s Studio who had fled from L.A. to New York during the 1950s after he was blacklisted from Hollywood for refusing to testify against coworkers in anti-Communist hearings; met wife when he took over for Jason Robards as Hickey in NYC production of "The Iceman Cometh" in the late 1950s; died in 1998 at the age of 77
- mother Eileen Ryan: Gave up a flourishing stage career to raise her sons; resumed acting career in the late 1980s, appearing in films like "Parenthood" (1989), Penn's "The Indian Runner" (1991), and "Magnolia" (1999)
- brother Michael Penn: Born Aug. 1, 1958; wrote score for "Boogie Nights" (1997); married to singer-songwriter Aimee Mann
- brother Christopher Penn: Born Oct. 10, 1965; acted together in "At Close Range" (1986); died Jan. 24, 2006 from cardiomyopathy, an enlarged heart with multiple prescribed medications at age 40
- daughter Dylan Francis Penn: Born April 13, 1991 in Los Angeles; mother, Robin Wright
- son Hopper Jack Penn: Born Aug. 6, 1993; mother, Robin Wright; named after Dennis Hopper and Jack Nicholson
Companions
- Elizabeth McGovern: met on set of "Racing With the Moon"; engaged c. 1983-84; separated in 1984
- Pam Springsteen: sister of Bruce Springsteen
- Susan Sarandon: together briefly in 1984; later co-starred together in "Dead Man Walking" (1995)
- Jewel: no longer together; born c. 1974
