Kline began his career on stage in 1972 with The Acting Company. He has gone on to win three Tony Awards for his work on Broadway, winning Best Featured Actor in a Musical for the 1978 original production of On the Twentieth Century, Best Actor in a Musical for the 1981 revival of The Pirates of Penzance, and Tony Award for Best Actor in a Play for the 2017 revival of Present Laughter.

He made his film debut opposite Meryl Streep in Sophie's Choice. For his role in the 1988 comedy hit A Fish Called Wanda, he won the Academy Award for Best Supporting Actor. In 2003, he starred as Falstaff in the Broadway production of Henry IV, for which he won the Drama Desk Award for Outstanding Actor in a Play.

He has been nominated for an Emmy Award, two BAFTA Awards and five Golden Globe Awards. His other films include The Big Chill, Silverado, Cry Freedom, Dave, The Hunchback of Notre Dame, The Ice Storm, In & Out, The Road to El Dorado, De-Lovely, My Old Lady, and Beauty and the Beast. Since 2011, Kline has had a recurring role on the animated comedy series Bob's Burgers.

He has won an Academy Award and three Tony Awards and is a 2003 American Theatre Hall of Fame inductee.

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