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Over his career as a television director, Leo Penn helmed well over 400 primetime hours on a wide variety of series, ranging from Star Trek to I Spy to Diagnosis Murder. In 1973, he received an Emmy for directing a two-hour episode of Columbo titled "Any Port in a Storm." Before becoming a director, he acted on stage and in a few feature films, beginning with Shame (1945). His film career had just begun when Penn was blacklisted after attending a pro-union meeting with other actors. That the group was actively supporting the first blacklistees, the Hollywood Ten, only worsened matters. Unable to work in film, he turned to Broadway; there, along with his wife Eileen Ryan, he starred in several productions, including The Iceman Cometh, Cat on a Hot Tin Roof, and Of Mice and Men. He also found acting jobs on television. In 1959, he returned to the screen in The Story on Page One, but by then the acting profession had lost its luster and he decided to become a director. He had his first helming job on the early-'60s medical drama Ben Casey. In the mid-'90s, Penn reentered feature films as an actor, appearing with his wife in his son Sean Penn's directorial debut The Crossing Guard (1995). Son Sean also produced the last play in which Penn performed, a 1997 production of Remembrance. Though Sean is most famous, Penn's other sons, Michael Penn and Chris Penn, are also in the entertainment industry, Michael as a singer/songwriter and Chris as an actor.

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