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20 Entertainment Flops in Boomer History

Truly great times had some cringe-worthy music, movies, TV shows and books

  • Gigli. Biggest Entertainment Flops.

    'Gigli' (2003)

    En español | Beverly Hills Cop, Midnight Run, Scent of a Woman ­— Martin Brest directed some fab films. But his romantic comedy about two kidnappers (Ben Affleck and Jennifer Lopez) who fall in love was, according to the Wall Street Journal, “the worst movie ... of our admittedly young century.” Box office didn't even cover the two stars’ reported take of $25 million. — Columbia Pictures/Everett Collection

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  • Geraldo Rivera: The Mystery of Al Capone's Vaults. Biggest Entertainment Flops.

    'The Mystery of Al Capone’s Vaults' (1986)

    Who could forget one of the most hyped events ever on the tube? In the build-up to his two-hour special, Geraldo Rivera promised to reveal the secrets of the Prohibition-era gangster’s secret hiding place. Some 30 million viewers tuned in for the first glimpse of … dirt. — Everett Collection

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  • Jimi Hendrix as opening act for The Monkees. Biggest Entertainment Flops.

    The Jimi Hendrix-Monkees Tour (1967)

    Hendrix’s manager thought the psychedelic guitar hero would get great exposure as the opening act for a fake rock quartet created for a TV sitcom. But with prepubescent fans drowning out “Purple Haze” with cries of “We want Davy!” Hendrix quit after seven painful concerts. — Michael Ochs Archives/Getty Images

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  • My Mother the Car. Biggest Entertainment Flops.

    'My Mother the Car' (1965)

    Jerry Van Dyke might still be kicking himself. He turned down the title role in Gilligan’s Island to star in a TV sitcom about a guy who purchases a dilapidated car that turns out to be his reincarnated mother. No surprise, it was gone after a single season. — United Artists/Everett Collection

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  • Can't Stop the Music. Biggest Entertainment Flops.

    'Can't Stop the Music' (1980)

    The disco-era movie disaster inspired the annual Razzies award for the worst in film. Still, we got to see not only the Village People on the big screen but also Olympic great (and now Kim Kardashian’s stepdad) Bruce Jenner, who cavorted in hot pants and a crop top. — Anchor Bay/Everett Collection

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  • Prince's Unpronounceable Symbol. Biggest Entertainment Flops.

    The Name Formerly Known as Prince (1993-2000)

    In a dispute with his record label, according to Rolling Stone, the diminutive, purple-loving R&B star abandoned his given name for an unpronounceable symbol. After the media started calling him “the artist formerly known as …” he became “Prince” again. — Kevin Mazur/WireImage/Getty Images

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  • Carrie: The Musical. Biggest Entertainment Flops.

    'Carrie: The Musical' (1988)

    The 1976 movie based on Stephen King's horror novel was a huge hit, but setting a ritual pig slaughter to music seems a notion only a writer for The Simpsons would dream up. The show closed after five performances and lost $8 million, the biggest Broadway flop of its time. — Time & Life Pictures/Getty Images

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  • Greg Allman and Cher. Biggest Entertainment Flops.

    'Two the Hard Way,' by Greg Allman and Cher (1977)

    Though the Southern rocker and pop diva — then married — created a critical and commercial disaster, a rare surviving vinyl copy will cost you $84.99 on Amazon today. — Terry O'Neill/Getty Images

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  • Cop Rock. Biggest Entertainment Flops.

    'Cop Rock' (1990)

    Producer Steven Bochco followed up his brilliant Hill Street Blues TV police drama with an inexplicable series that featured singing and dancing boys in blue. Slate called it “the weirdest network TV show of the modern era.” — 20th Century Fox/Everett Collection

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  • Milli Vanilli. Biggest Entertainment Flops.

    Milli Vanilli (1989)

    Not until after the handsome duo won a Grammy for best new artist did the world discover they were lip-synching in concert and anonymous studio vocalists had recorded their hits. Stripped of their award, the pair couldn’t leave bad enough alone and released a record entitled The Real Milli Vanilli. It bombed. — Michael Ochs Archives/Getty Images

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  • Jackie Gleason: You're in the Picture. Biggest Entertainment Flops.

    'You're in the Picture' (1961)

    In what seemed like an imitation of Groucho Marx and You Bet Your Life, Jackie Gleason tried his hand at a TV game show. The premiere was so bad that for the second, and final episode, Gleason sat in front of a camera for 30 minutes and apologized. — Everett Collection

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  • Adventures of Pluto Nash. Biggest Entertainment Flops.

    'Pluto Nash' (2003)

    Back when Eddie Murphy (here with costars Rosario Dawson and Randy Quaid) was a box-office force, a sci-fi comedy adventure loaded with expensive special effects had to seem like a good wager to producers. They were so wrong that even Murphy declined to promote the debacle. — Warner Bros/Everett Collection

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  • Moose Murders. Biggest Entertainment Flops.

    'Moose Murders' (1983)

    Some consider this the Broadway bomb against which all others must be measured. New York Times theater critic Frank Rich wrote, “Let's not review its contents here except to say that it was a comedy whose climax consisted of a gauze-wrapped quadriplegic rising from his wheelchair to kick a man wearing a moose costume in the groin.” — Ruby Washington/The New York Times/Redux Pictures

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  • William Shatner's The Transformed Man. Biggest Entertainment Flops.

    'The Transformed Man,' William Shatner (1968)

    Star Trek’s Captain Kirk had hubris, or perhaps a sense of humor. He not only covered the Beatles’ “Lucy in the Sky With Diamonds” and Bob Dylan’s “Mr. Tambourine Man,” but he did it in a spoken-word style reminiscent of Rex Harrison in My Fair Lady. Listeners may have thought they were hallucinating. — CBS/Getty Images

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  • The Brady Brides. Biggest Entertainment Flops.

    'The Brady Brides' (1981)

    Among many terrible TV spinoffs (The Lone Gunmen and Beverly Hills Buntz come to mind), this might have been the worst. Brady sisters Jan and Marcia get married, and the two couples share a house. The show lasted 10 episodes, “about the length of a typical Hollywood marriage,” Entertainment Weekly joked. — Paramount Television/Everett Collection

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  • Rosie Magazine. Biggest Entertainment Flops.

    'Rosie' Magazine (2000-2002)

    After fellow daytime talk show host Oprah Winfrey launched her successful eponymous magazine, Rosie O’Donnell and the publisher of McCall’s partnered to rebrand the venerable women’s journal as Rosie. O’Donnell eventually pulled the plug and set off some nine-figure litigation. — Marty Lederhandler/AP Photo

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  • Supertrain. Biggest Entertainment Flops.

    'Supertrain' (1979)

    Imagine a radioactive version of The Love Boat. NBC somehow saw a potential hit in a TV show about the goings-on aboard a nuclear-powered bullet train. Reportedly one of the most costly series ever, it helped to nearly bankrupt the network. — NBC/Everett Collection

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  • A Million Little Pieces by James Frey. Biggest Entertainment Flops.

    'A Million Little Pieces,' by James Frey (2003)

    This addiction memoir was a huge best-seller. Then Internet sleuths exposed that much of the book was a fabrication and Oprah lambasted Frey on national TV. After a bunch of litigation, the publisher offered a refund to readers who felt cheated. — Tim Boyle/Getty Images

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  • Cutthroat Island. Biggest Entertainment Flops.

    'Cutthroat Island' (1995)

    This swashbuckler, starring Matthew Modine and Geena Davis, was the biggest movie flop ever, losing an inflation-adjusted $147 million. Perversely, less than a decade later, Disney’s markedly similar Pirates of the Caribbean movies were huge hits. — MGM/Everett Collection

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  • Total Recall: My Unbelievably True Life Story by Arnold Schwarzenegger. Biggest Entertainment Flops.

    'Total Recall: My Unbelievably True Life Story,' by Arnold Schwarzenegger (2012)

    The actor-turned-politician-turned-actor received an advance of several million dollars, reported the German newspaper Spiegel. His book sold about 50,000 copies — not too shabby, unless you consider that’s a tenth of the sales of a book by an actual action hero, the SEAL who helped kill Osama bin Laden. — Hannelore Foerster/Getty Images

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