01. Howard Keel as Gaylord Ravenal in Showboat
02. Robert Preston as Harold Hill in The Music Man
03. Richard Beymer as Tony in West Side Story
04. James Cagney as George M. Cohan in Yankee Doodle Dandy
05. Tim Curry as Dr. Frank-N-Furter in The Rocky Horror Picture Show
06. Harve Presnell as Johnny Brown in The Unsinkable Molly Brown
07. Gordon MacRae as Curly McLain in Oklahoma!
08. Gene Kelly as Don Lockwood in Singin' in the Rain
09. Rossano Brazzi as Emile de Becque in South Pacific
10. Cliff Richard as Don in Summer Holiday
11. Marlon Brando as Sky Masterson in Guys and Dolls
12. Rick Moranis as Seymour Krelborn in Little Shop of Horrors
13. Bing Crosby as C. K. Dexter-Haven in High Society
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13 more leading men in musicals (no repeats).
14. Fred Astaire as Tom Bowen in Royal Wedding
15. Ewan McGregor as Christian in Moulin Rouge (2001)
16. Frank Sinatra as Robin in Robbo and the 7 Hoods
17. James Stewart as Ted Barker in Born to Dance
18. Tommy Steele as Arthur Kipps ("Artie") in Half a Sixpence
19. Louis Jourdan as Gaston Lachaille in Gigi
20. Maurice Chevalier as Danilo in The Merry Widow (1934) (altered by Hollywood from operetta to musical)
21. Hugh Jackman as Jean Valjean in Les Misreables
22. Clint Eastwood as Sylvester Newel in Paint Your Wagon
23. Gerard Butler as The Phantom in The Phantom of the Opera
24. Nelson Eddy as Paul Allison in Maytime
25. Rex Harrison as Professor Henry Higgins in My Fair Lady
Nelson Eddy was repeated. I already took out my own entry for Nelson Eddy to accommodate yours. No repeats of leading man or movie.
You know what? You are a pain in the ass.