5. Celebrity: LL Cool J
Clothing line: LL Cool J for Sears
Launch date: 2008
Fail date: 2009
Reasons for the fail: The launch of LL’s line for Sears coincided almost exactly with the economy’s swift plummet, and barely six months after his line of glittery hoodies and other back-to-school style sportswear debuted, it was gone, taking it with it a whole slew of ads featuring LL, his wife Simone and their four children. Poor kids.

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