milli vanilli

This R&B duo sold millions of records in the late ‘80s to early ‘90s, and even won a Grammy for best new artist. However, during a live segment on MTV, Milli Vanilli’s music track skipped and revealed that they weren’t even singing, resulting in a huge media exposé, lawsuits, and their Grammy being revoked.

natalia kills

On New Zealand's version of “The X Factor,” singer and judge Natalia Kills went on a bizarre rant against contestant Joe Irvine, calling him "a laughing stock" and accusing him of copying her husband, singer Willy Moon, who was also a judge. Viewers were disgusted, and Kills and Moon were removed from the show.

ashlee simpson

Ashlee Simpson’s career was on the rise in 2004 when she netted a performance on “Saturday Night Live.” However, a technical hiccup on “SNL” revealed that she was lip syncing, and instead of saving her act, Simpson danced an awkward jig and left the stage, resulting in ridicule and a ruined career.

doug williams

During a roast of football player Emmitt Smith, comedian Doug Williams had his set interrupted by host Jamie Foxx, who mocked Williams’ jokes and basically told him to get off the stage. The strange, hilarious, and completely unscripted incident caused Williams and his career to bomb.

jackie mason

Comedian Jackie Mason’s gig on “The Ed Sullivan Show” ended before it truly began when he held up his middle finger on live TV. A furious Ed Sullivan allegedly told Mason, “I will destroy you in show business,” a quote which unfortunately proved to be true for Mason, though his entertainment career is still going.