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“West Side Story” (1957)
The classic Leonard Bernstein musical, with a book by Arthur Laurents and lyrics by a young Stephen Sondheim, lost out at the 12th Tony Awards — to Meredith Willson’s “The Music Man.”
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“Gypsy” (1959)
Two years later, another Laurents-Sondheim collaboration (this time with composer Jule Styne) lost out to two rivals that tied for the award: the mostly forgotten “Fiorello!” and the Rodgers & Hammerstein classic “The Sound of Music.” But while “Gypsy” has seen four revivals in the years since, “Sound of Music” has returned to Broadway only once — and “Fiorello!” not at all.
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“Hair” (1968)
Galt MacDermot’s seminal rock musical was an influential hit, but it lost the top prize to the more buttoned-up historical pageant “1776.”
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“Grease” (1972)
Tony voters rewarded MacDermott three years later for the now forgotten “Two Gentlemen of Verona” — and snubbed not just the popular ’50s-set “Grease,” but also Sondheim’s “Follies.”
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“Chicago” (1975)
John Kander and Fred Ebb’s caustic look at fame was overshadowed by “A Chorus Line” — but the 1996 revival is still running after two decades and led to the Oscar-winning 2002 big-screen adaptation.
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“Dreamgirls” (1981)
I am telling you, guess who’s not going to the Tony stage despite becoming a much-loved hit. The R&B show that made Jennifer Holliday a major star lost to Maury Yeston’s more esoteric “Nine,” based on Federico Fellini’s movie “8 1/2.”
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“Into the Woods” (1987)
Stephen Sondheim’s much-loved fairy tale mash-up has become a fan favorite, but it lost the Best Musical race to a genuine behemoth: Andrew Lloyd Webber’s “The Phantom of the Opera.”
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“Miss Saigon” (1991)
Alain Boublil & Claude-Michel Schönberg Vietnam-set update of “Miss Saigon” (complete with onstage helicopter) amazingly lost to the lightweight “The Will Rogers Follies.”
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“Mamma Mia!” (2001)
The ABBA jukebox musical was a hit that spawned two movies, but it lost to Jeanine Tesori’s adaptation of the 1967 Julie Andrews film “Thoroughly Modern Millie.”
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“Wicked” (2003)
In one of the biggest upsets in Tony history, Stephen Schwartz’s anthem-filled prequel to “The Wizard of Oz” lost the Best Musical prize to the R-rated puppets of “Avenue Q.”