-Married to Robin Wright Penn (27 April 1996 - present) 2 children

-He served 32 days in jail in 1987 for hitting an extra.

-He and Robin Wright Penn lived together from 1991 until their marriage in 1996. They had two children before their marriage.

-Appeared with his brother Chris Penn in At Close Range (1986), in which their actress mother, Eileen Ryan, played their grandmother.

-Brother of actor Chris Penn and musician Michael Penn, son of Leo Penn and Eileen Ryan.

-Moved to Marin County (North of San Francisco) to avoid raising his kids in Hollywood.

-Daughter, with Robin Wright Penn, Dylan Frances (b. 13 April 1991).

-Son, with Robin Wright Penn, Hopper Jack (b. 6 August 1993). Named after two family friends, Dennis Hopper and Jack Nicholson.

-Quit smoking (or at least cut down) on his 40th birthday for health reasons. Prior to that, he was known as one of Hollywood's heaviest smokers, smoking at least four packs a day.

-Dated Musician and actress Jewel Kilcher for a time. He directed the music video for her song "You Were Meant For Me" in 1997.