Believe me, I realize there are many, many "worthy" candidates.
My pick is the infamous "Breakfast at Tiffanys" that starred (then) hot TV stars Mary Tyler Moore and Richard Chamberlain in 1966 with score by the esteemed Bob Merrill and book by Abe Burrows. Let's add legendary David Merrick was the producer.
Where to even start?
David Merrick had the book by Burrows scrapped when it didn't click with the out of town tryout audiences.
So he hires...drumroll...EDWARD ALBEE...to rewrite the book. "Who's afraid of Virgina Woolf" Edward Albee. Edward admits now he didn't know what he was doing, and according to Richard Chamberlain it was a "dark musical" that the audience hated, with material rewritten hours before the cast would do a performance. According to Chamberlain, Mary was crying offstage between performances.
After four NY preview performances David Merrick pulled the plug, despite huge advance sales, refunding all the money. What makes this my all time worst flop was that David Merrick actually took out ad space in the NY times where he explained the closing was due to “rather than subject the drama critics and the public to an excruciatingly boring evening.”
This makes Spider Man the musical look child's play in comparison.
Any other flops in this pantheon one can think of?
"when I’m on stage I see the abyss and have to overcome it by telling myself it’s only a play." - Helen Mirren
"Hampered by scathing reviews, and despite the fact that the theatre was sold out every night,the financial backers pulled their money out of the show, and it closed on May 15 after only 16 previews and 5 performances, guaranteeing its place in theatre history as one of the most expensive disasters of all time. According to The New York Times, the "more-than-$7 million show...was the most expensive quick flop in Broadway history."
Carrie had a decent run off-broadway a few years ago with some notable people, so it's not the worst thing ever, but that original production sounds pretty awful.
"Via Galactica" back in the 70's is legendary because the rock opera, which was set in the future in an asteroid was deemed by even it's producers as so incomprehensible that additional plot synopses were inserted into the Playbills. It closed after 7 performances.
It sounded like epic surreal roadkill, with trampolines on stage to convey weightlessness in space.
"when I’m on stage I see the abyss and have to overcome it by telling myself it’s only a play." - Helen Mirren
I'd like to offer up Into The Light - the first and only musical about the Shroud of Turin. Starring Dean Jones, it opened in 1986 to scathing reviews and closed after 6 performances.
I didn't see it, but everything I've read and heard about it suggests that it was ghastly.
"You drank a charm to kill John Proctor's wife! You drank a charm to kill Goody Proctor!" - Betty Parris to Abigail Williams in Arthur Miller's The Crucible
From what I hear, Dude was so bad that George Ragni, the man who wrote the book and lyrics to the show, yelled at audience members who tried to leave at intermission to "go sit down and suffer with everybody else. Suffer!" so that might take the cake.
There's Kelly and The Little Prince and the Aviator too.
It got generally favorable reviews. It failed to catch on. It has been performed regionally and with the right cast could be ripe for a full scale revival. If flops like Gigi and Sideshow get one, this would be one that deserves a second chance. I saw many of the flops listed here and Superman. Superman does not belong in that class.
Talk legendary and the name Rachel Lily Rosenbloom and Senator Joe come to mind. Saw Rachel and it was a god awful mess. It was like watching Gomez in the TV series The Addams Family waiting for his toy trains to collide & collide they did on stage.
I too saw many of the flops listed here, including both Via Galactica and Dude. My worst was, Got Tu Go Disco. Now, that was a flop in a class of its own.
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