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."
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.
Galt MacDermot's seminal rock musical was an influential hit, but it lost the top prize to the more buttoned-up historical pageant "1776."
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."
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.
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."
"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."
"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."
"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."
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."