By definition, "flops" aren't (necessarily) artistic failures, but financial ones. No matter how great a show is, it is still a flop if it doesn't earn back its initial investment. Most of Sondheim's shows (including ANYONE CAN WHISTLE, FOLLIES, PACIFIC OVERTURES, MERRILY WE ROLL ALONG, SUNDAY IN THE PARK WITH GEORGE, and PASSION), lots of Tony and Pulitzer winning plays, and even some Tony winning Best Musicals (HALLELUJAH BABY!, PASSION, SUNSET BOULEVARD, TITANIC, THOROUGHLY MODERN MILLIE) were flops -- even though some of them were terrific critically acclaimed. They just -- for whatever reason -- didn't find an audience.
Now a "trainwreck" doesn't have an "offical" definition, but it does seem to imply a show that was a complete disaster -- artistically AND financially -- that also had an extremely short run (CARRIE, MOOSE MURDERS, BRING BACK BIRDIE ETC.....) ...... I personally wouldn't call something like the Pulitzer and Tony winning plays ANGELS IN AMERICA or I AM MY OWN WIFE, or the Pulitzer-winning SUNDAY IN THE PARK or the Tony winner MILLIE (or SIDESHOW or CAROLINE) a "trainwreck, although they all certainly were flops....... but maybe that's just me.....
"What a story........ everything but the bloodhounds snappin' at her rear end." -- Birdie
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"The Devil Be Hittin' Me" -- Whitney