Bosley played the Knave of Hearts in a Hallmark Hall of Fame telecast of Eva Le Gallienne's production of "Alice in Wonderland" in 1955. But his career began in a stage role based on New York City mayor Fiorello H. La Guardia in the long Broadway musical "Fiorello!" (1959), for which he won a Tony Award. In 1994, Bosley originated the role of Maurice in the Broadway version of Disney's "Beauty and the Beast". Bosley also toured as Cap'n Andy in Harold Prince's 1994 revival of "Show Boat".
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