by Ken Mandelbaum, full article can be found
here afew of my favorites...
1954: Dolores Gray wins the musical-actress Tony for Carnival in Flanders, a show that ran just six performances. It remains to this day the shortest-lived Tony-winning performance.
1956: Lotte Lenya wins the supporting-musical-actress Tony for The Threepenny Opera, the only time in Tony history when a prize was won by a performer in an off-Broadway show. Of course, Lenya was magnificent. But how was she considered eligible?
1985: The season is so poor that the Best Musical Actor and Actress categories are eliminated, along with the prize for choreography.
1994: A Grand Night for Singing, a compilation of Rodgers and Hammerstein songs with no spoken dialogue, somehow gets a nomination for Best Book.
1953: Thomas Mitchell wins the Tony for Best Actor in a Musical for Hazel Flagg, even though he does no singing or dancing in the show. One can point to a number of other performers who won or were nominated for songless roles: Ballerina Natalia Makarova got a Tony for On Your Toes in 1983. Tapper Savion Glover was nominated for Noise/Funk (1996). And Karen Ziemba and Boyd Gaines didn't sing in but won Tonys for Contact (2000). But Makarova, Glover, Ziemba, and Gaines all danced in their shows, thus offering more genuinely "musical" performances than Mitchell's.
1954: A Tony for Kismet goes to Russian composer Alexander Borodin, who died in 1887. Themes from Borodin were developed by Robert Wright and George Forrest into the score for the Broadway hit.
1960: Gypsy, now considered to be among the finest of all Broadway musicals, loses in all categories in which it's nominated. A similar case: Chicago loses in eleven 1976 Tony categories. ('76 was the year of A Chorus Line.)
1963: Stephen Sondheim doesn't even get a nomination for his first full score for Broadway, for A Funny Thing Happened on the Way to the Forum. But Milton Shafer and Ronny Graham do get nominated that year, for the score for the short-lived flop Bravo Giovanni.
1965: An inexplicable prize: Neil Simon wins as best author of a play, for The Odd Couple, but the Best Play award goes to The Subject Was Roses, written by Frank Gilroy, who lost to Simon in the author category. That best-author category is never heard from again.
1967: Already insecure Apple Tree star Barbara Harris is further shaken when gatecrasher Stan Berman takes to the stage during Harris's acceptance speech and plants a kiss on her cheek.
1969: Playing what's quite obviously the leading role of John Adams in 1776, William Daniels declines his featured-musical-actor nomination. Actors billed below the title, like Daniels, were still strictly relegated to supporting categories.
1971: Larry Kert is nominated for Company, the only time in Tony history where a replacement performer received a performance nomination. Kert succeeded Dean Jones shortly after the opening.
1971: The score award is divided into two separate categories, for music and lyrics; Stephen Sondheim takes both prizes, for Company.
1975: John Kani and Winston Ntshona are ruled eligible to compete as a single performance for their work in Sizwe Banzi Is Dead and The Island---and they win. In 1998, Alice Ripley and Emily Skinner would be ruled similarly eligible as a single performance, for their work in Side Show. They do not win.
1975: Jerry Herman's toe-tapping score for Mack and Mabel isn't nominated, but the scores for the forgotten Letter for Queen Victoria and The Lieutenant are.
1977: Dead twenty-seven years, Kurt Weill gets a nomination, for his Happy End score.
1982: Amanda Plummer is nominated in both the leading and featured actress categories, and wins for Agnes of God, the featured performance. In 2002, Kate Burton is similarly nominated in the best-actress and featured-actress categories (for Hedda Gabler and The Elephant Man), but does not win in either.
1983: Eighteen years after his death, T.S. Eliot wins a best-book Tony, for Cats.
1995: Only two new musicals open on Broadway, and one of them, Smokey Joe's Cafe, is a revue made up of old songs. With Sunset Boulevard the only musical with a book and a new score, it easily takes the best-musical prize. And Sunset Boulevard is the unopposed winner in the book and score categories.
1996: One of the biggest brouhahas in Tony history: Big-budget musicals like Victor/Victoria and Big are left out of the best-musical nominations. When nothing in Victor/Victoria is nominated except Julie Andrews, the star declines her nomination. Although Andrews' name remains on the ballot, she loses to Donna Murphy in The King and I.
1999: As with Jerome Robbins' Broadway in 1989, the Best Musical Tony goes to Fosse, a compilation of pre-existing material in pre-existing staging.
2000: More controversial is the best-musical prize to Contact, a dance piece with no live singing, performed to pre-recorded tracks.