STEVE INSKEEP, host:

When you have high expectations, a lot of hype and financial failure, you often end up with a flop. And this week in a four-part series, we'll be celebrating famous flops in entertainment. We'll hear an anatomy of a flop, how Hollywood types cope with failure. We'll look at flops that flipped, things that had first failed that went on to become classics. To kick off our series, NPR's Elizabeth Blair takes a look at some famous flops and why we love them.

ELIZABETH BLAIR reporting:

The first known use of the word `flop' as a verb, meaning fail, was in P.G. Wodehouse's novel "A Damsel in Distress." Erin McKean is editor in chief of the Oxford American Dictionary.

Ms. ERIN McKEAN (Editor in chief, Oxford American Dictionary): His citation is from 1919, and it's a theatrical context: `The summertime number flopped on the second night.'

BLAIR: In 1937, "A Damsel in Distress" became a big-budget movie musical starring Fred Astaire and songs by George and Ira Gershwin.

(Soundbite of "A Damsel in Distress")

Unidentified Singers: (Singing) Holding hands a midnight 'neath the starry sky, nice work if you can get it, and you can get it if you try.

BLAIR: But "Damsel" flopped. Some say that's because Fred danced without Ginger. Broadway's had plenty of flops. There's the infamous "Carrie, the Musical," which lost its investors over $7 million in the late 1980s, or more recently the much-ballyhooed "Taboo," the show based on the life of pop star Boy George.

(Soundbite of "Taboo")

Unidentified Actor: (Singing) Do you really want to hurt me? Do you really want to make me cry?

BLAIR: "Taboo" was produced and financed by Rosie O'Donnell, and she lost about $10 million doing it. Peter Marks, theater critic for The Washington Post, believes "Taboo" was one of those shows that shouldn't have been on Broadway in the first place.

Mr. PETER MARKS (Theater Critic, The Washington Post): It probably would have done quite well in a small, like, dark theater space somewhere with all that wonderful Boy George music. So sometimes it's just that simple. It may be the right time but just the wrong place.

BLAIR: The wrong cast is another ingredient of a flop. Take the 1993 TV sitcom "It Had to be You." Faye Dunaway played a magazine editor dating a single father of three boys. Jenny Bicks, an executive producer on "Sex and the City," was a writer on "It Had to be You." She says viewers could not see the star of "Bonnie & Clyde" being a lighthearted stepmom.

Ms. JENNY BICKS (Writer, "It Had to be You"): And we would get notes like, `Please don't have any scenes with her and the boys together,' which was kind of hard because that was basically the show.

BLAIR: CBS yanked it after just four episodes. Hollywood lore is littered with megaflops. One famous example is "Ishtar," which lost Columbia Pictures nearly $40 million. Another was the ill-fated movie version of "Bonfire of the Vanities," based on the huge best-seller by Tom Wolfe.

(Soundbite of "Bonfire of the Vanities")

Mr. TOM HANKS: (As Sherman McCoy): We should move up here. Have you ever thought? I mean, what if we moved out of New York?

BLAIR: A lot went wrong with the film Brian De Palma directed for Warner Bros. In her book, "The Devil's Candy," Julie Salamon says, for starters, studio executives watered down Wolfe's social satire for the big screen.

Ms. JULIE SALAMON: The whole point of "Bonfire of the Vanities," the book, was to be offensive. It offended everybody: rich people, white people, black people. It was an equal opportunity offender. And, you know, the studio got nervous.

BLAIR: So they made changes, often against Brian De Palma's will. For example, they changed a white Jewish judge working in a racially mixed borough to a black judge played by Morgan Freeman.

(Soundbite of "Bonfire of the Vanities")

Mr. MORGAN FREEMAN (As Judge Leonard White): All right, Mr. Lockwood. You sit down. And if and when your lawyer deigns to grace us with his presence...

Mr. SHIEK MAHMUD-BEY (As Lockwood): Two to six, judge.

Mr. FREEMAN: I beg your pardon?

Mr. MAHMUD-BEY: Two to six.

Ms. SALAMON: There was a lot of pressure from the studio executives to tone things down to make them more politically correct.

BLAIR: Add to that the enormous anticipation surrounding "Bonfire," since just about everyone in the media had read Tom Wolfe's book. Critics were venomous. Audiences stayed away and "Bonfire" bombed. If there's anyone who knows about living through a flop, it's Steven Bach. He was one of the executives at United Artists who signed off on a movie called "Heaven's Gate."

Mr. STEVEN BACH (United Artists): I think a flop has to be such an enormous event in which the expectations that have been aroused by publicity or the director or the stars are so little met it makes the movie in question seem to stand for something larger than itself.

BLAIR: "Heaven's Gate" was written and directed by Michael Cimino, whose movie "The Deer Hunter" had just won five Academy Awards. Cimino made "Heaven's Gate" on a lavish scale, including an extended dance sequence shot at enormous expense in Oxford, England.

(Soundbite of "Heaven's Gate")

BLAIR: In some ways, what happened with "Heaven's Gate" is just the opposite of "Bonfire of the Vanities," where the studio interfered too much. Steven Bach says in this case the studio lost control.

Mr. BACH: The big misstep that we made was believing the director when he said, `I can make this movie for $12 million.' He couldn't and he didn't. He made it for three times that.

BLAIR: "Heaven's Gate" ended up losing some $44 million. Steven Bach resigned. He went on to write a book about the experience called "Final Cut." United Artists was sold off by its corporate owners.

Some films are labeled `flop' unjustly. There was Kevin Costner's "Waterworld," nicknamed "Kevin's Gate," and Elizabeth Taylor's notoriously overbudgeted "Cleopatra." Both eventually turned a profit. Others really do lose money and go on to become punch lines, like J. Lo and Ben Affleck's "Gigli." Steven Bach has a theory on why people seem to relish a good flop.

Mr. BACH: There is a need to slap down yesterday's hero, and that was true with "Heaven's Gate." A lot of the critics seemed to feel, `We said too many nice things about "The Deer Hunter" and we didn't really mean them. So we'll--we're going to take them away now.'

BLAIR: TV writer and producer Jenny Bicks believes people are fascinated with flops because they know it could have been them.

Ms. BICKS: Everybody wants to see somebody fail because it makes them feel like they're not the only ones who have it in them. Anyone is capable of making a mistake.

BLAIR: After watching the "Bonfire" debacle unfold, Julie Salamon says it's a miracle good movies ever get made at all.

Elizabeth Blair, NPR News.

INSKEEP: This is MORNING EDITION from NPR News. I'm Steve Inskeep. Transcript provided by NPR, Copyright NPR.