Alaimo is a classically trained theatre actor, and performed as part of the Marquette University Players and the Milwaukee Repertory Theater in the 1960s in everything from Shakespeare and the classics to world premiere productions. He was also a member of various theatre companies in New York and touring companies across the country before making the move to Los Angeles in 1973. Some of his theatrical roles include Iago in Othello, Rodolpho in Arthur Miller's A View From the Bridge and Lucky in Samuel Beckett's Waiting for Godot.
Alaimo has been playing characters in television shows since 1971. He has appeared, mostly as villains, in shows such as The Doctors, Kojak, Gunsmoke, Baretta, The Six Million Dollar Man, The Bionic Woman, Starsky & Hutch, Knight Rider, Quincy, The Greatest American Hero, The Incredible Hulk, Quantum Leap, Family Guy, Walker, Texas Ranger, Wonder Woman, The Rockford Files, Hill Street Blues, Barnaby Jones, and The A-Team. Alaimo has appeared in some feature films including the 1984 science fiction movie The Last Starfighter (portraying the human guise of an alien assassin), the Leslie Nielsen film Naked Gun '"`UNIQ--templatestyles-0000000D-QINU`"'33+1⁄3: The Final Insult, Tango & Cash, and the 1988 film The Dead Pool. He also appeared as Curtis Block in the television movie Case Closed and as a security officer on Mars in the Arnold Schwarzenegger movie Total Recall.
He played several characters in Star Trek: The Next Generation (Star Trek: TNG), starting in the first season. He has the distinction of two firsts on Star Trek: TNG, playing the first Romulan, Commander Tebok, in the 1988 episode "The Neutral Zone", and the first Cardassian (in any Star Trek series), Gul Macet, in the 1991 episode, "The Wounded". He also played a poker player who speaks French to Data in the episode "Time's Arrow". In 1993, Alaimo began playing Cardassian character Gul Dukat in Star Trek: Deep Space Nine. Gul Dukat was a recurring character that appeared in 33 episodes of that series.

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