A life member of
The Actors Studio, Penn won the
Theatre World Award in 1954 for his performance in the play
The Girl on the Via Flaminia. He acted in numerous roles in the early years of television. In 1956, he was cast as Mr. Rico in the episode "Ringside Padre" of the religion anthology series
Crossroads. In 1957, he appeared in the episode "One If by Sea" of the military drama series,
Navy Log. He was also cast in an episode of
Beverly Garland's 1957–1958 groundbreaking crime drama
Decoy. In 1960, he played Cavage in "The Poker Fiend" on
Richard Boone's
CBS western series
Have Gun – Will Travel. In 1961, he was cast as Tiko in the episode "The World Is Her Oyster" of the
ABC adventure series
The Islanders, set in the South Pacific, and appeared in an episode of the ABC crime drama
The Asphalt Jungle. He also appeared in another ABC adventure series
Straightaway, which focuses on automobile racing. On March 3, 1961, he co-starred with
Peter Falk and
Joyce Van Patten in the episode "Cold Turkey" of the ABC legal drama series
The Law and Mr. Jones starring
James Whitmore. About this time, he also appeared on
Pat O'Brien's ABC sitcom
Harrigan and Son. In the 1961–1962 television season, Penn acted in the CBS crime drama
Checkmate in the episode "The Button-Down Break" and starred as Jerry Green in
Gertrude Berg's CBS's sitcom
Mrs. G. Goes to College renamed at mid-season as
The Gertrude Berg Show. Penn landed work as a director for many television series, including
I Spy,
Lost in Space,
Cannon,
Star Trek,
Blue Light,
Custer, the 1976 western
Sara,
St. Elsewhere,
Kojak,
Starsky and Hutch,
Cagney & Lacey,
Little House on the Prairie,
Columbo,
Hawaii Five-O,
Trapper John, M.D.,
Hart To Hart,
Magnum, P.I., and
Father Murphy. In 1983, he was nominated for an
Emmy Award for Outstanding Directing in a Drama Series for
The Mississippi. ==Politics==