Jessica Simpson’s little sis was having a hard enough time gaining credibility in the pop world when this disastrous event occurred. On October 23, 2004, she took the stage of “Saturday Night Live” for what should have been a debutante ball of sorts. Her first song, “Pieces of Me,” went off without a hitch, but when her band launched into a second song, the vocals for “Pieces of Me” once again blared from the speakers, revealing to everyone in attendance – and the millions watching at home – that Simpson was lip-synching. A panicky Ashlee froze and grinned before doing an awkward hoe-down jig and bolting from the stage 30 seconds later. —Jeff Royer
(Photo: Frank Micelotta, Getty Images)
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