Biggest Tony upset of all time?

Im curious, what would be considered one of the bigger tony upsets? Now Im not asking in terms of who YOU thought should've won, but often as there is a usual consensus for who will win. For example, The Bands Visit and Hamilton are 2 recent clear favorites to take Best Musical. Can you imagine the upset if Mean Girls or Waitress took the win? Just wondering if there has been any fun cases of true shock of a winner.

Avenue Q over Wicked (or Caroline or Change).

I think La Cage aux Folles winning Score over Sunday was a big surprise to many.

I would hardly call KINKY BOOTS winning over MATILDA a huge upset. They were neck and neck all season.

Recent ones I can think of:

David Hyde Pierce in CURTAINS over Raul Esparza in COMPANY

LaChanze in THE COLOR PURPLE over Patti LuPone in SWEENEY TODD

THE PAJAMA GAME over SWEENEY TODD for Revival.

I also think Ruthie Ann Miles was a bit of a shock. She gave a beautiful performance and deserved the win, but most thought it was between Kuhn or Lucas in FUN HOME.

Updated On: 3/18/19 at 11:11 AM

I think Waitress could have won Best Musical if it didn't compete with Hamilton. Back in 2004, I think any of the best musical nominees would have won Best Musical in other seasons.

I really started paying attention to Broadway at around 2001 and the following is what I remember as upsets (not necessarily biggest Tony upset):

2004 Best Musical - Wicked was the big blockbuster musical that year but Avenue Q managed to win Best Musical, Best Book, and Best Original Score. I still think 2003-2004 season was one of the best Broadway ever had (Wicked, Avenue Q, Caroline or Change, Boy From Oz, Assassins, Taboo, etc.) I just remember going to both shows' rush lotteries that summer and both had huge crowds (not Hamilton ham4ham crowds but still a lot!)

2007 Best Leading Actor in a Musical - Raul Esparza was favored to win but David Hyde Pierce won.

2012 Best Leading Actor in a Play - Philip Seymour Hoffman was favored to win but James Corden won.

2017 Best Direction of a Musical - Michael Greif (Dear Evan Hansen) and Rachel Chavkin (Great Comet) were both favored to win but Christopher Ashley (Come from Away) won.

2018 Best Musical Revival - It was simply great to see Once on This Island win!!!!!! Even at the acceptance speech the producer stated he was surprised they won!

2018 Best Leading Actor in a Musical - People were generally surprised Tony Shalhoub won (there are other threads out there that discuss this already.) I'd say Joshua Henry and Ethan Slater were more favored than Tony to win last year.

Above are just a few examples of upsets but not sure if any would be the biggest tony upset of all time.

I didn't find Tony Shalhoub's win an upset at all.

The KINKY win was definitely an upset and a political situation when the British producers refused to share producing credits with established Broadway producers.

I forget, but wasn’t Steve Kazee winning for Once considered an upset also?

That and the whole pushing Bertie Carvel to Best Lead Actor, instead of featured in a ploy to win as many Tony's as possible. Add to that the pushing of the Matilda's for joint consideration, after the rules were already specifically changed after the Billy's won. Matilda's entire Tony campaign rubbed voters the wrong way and made voter feel as though they were expected to bow to the shows greatness. This was contrasted with Harvey Fierstein and Cyndi Lauper did anything and everything asked of them with a smile during the awards season for Kinky Boots. It was very much a literally example of "You catch more flies with honey then you do with vinegar" even if its a very high end balsamic.

CurtainPullDowner said: "I didn't find Tony Shalhoub's win an upset at all.

The KINKY win was definitely an upset and a political situation when the Britishproducers refused to share producing credits with established Broadway producers."

For me, the biggest Tony upset was Michael Arden not winning best direction for Deaf West Spring Awakening.

At the end of West Side Story, when Doc says that Maria is dead and Tony freaks out, that's probably the biggest Tony upset I've ever seen.

My first thought was Kinky Boots Vs Matilda. That was the first Tony's I watched, and I remember the HEATED debates on this board when Kinky won. Ive seen Kinky 4 times and haven't seen Matilda so I can't specifically comment on that show, but in terms of lead actor, I ebelvie the main argument was that Carvel should've been in supporting and that his role really was not a leading role. I can see why voters would vote for an equally excellent performance that is more of a demanding role over something that should be a supporting role. Just my two cents.