Harold Prince has won the most Tony Awards of all time, with 21 victories including special awards.
Prince’s total spans several sides of Broadway production. He won eight Tonys for directing a musical, eight for producing the season’s Best Musical, two as Best Producer of a Musical, and three Special Tony Awards. His winning productions included The Pajama Game, Fiorello!, Fiddler on the Roof, Cabaret, Company, Sweeney Todd, Evita, and The Phantom of the Opera.
The wording “including special awards” matters. Prince’s total is not limited to competitive category wins, and that broader count is why he stands above other major Tony figures. Tommy Tune, another all-around Broadway giant, has ten Tony Awards, while Stephen Sondheim holds the composer record rather than the overall record.
Prince’s career helped reshape the modern musical by pairing popular entertainment with ambitious subjects, including politics, marriage, antisemitism, and social conflict. He received a Lifetime Achievement Tony in 2006.