1. Britney Spears
How you remember her: We all fondly recall the early days of Britney Spears’ career when she wore a short skirt and pigtails in the “Baby One More Time” video. So much has changed since 1999 though, and while Brit-Brit has released albums consistently, she’s made horrible dating decisions, had a mental breakdown in 2007, had to have her father or manager (sometims boyfriend) look after her money, and then tried to resurface at the 2007 VMAs only to be unfairly ridiculed for her figure and her performance (okay, that part may have been warranted).
How you don’t want to remember her: For all intents and purposes, Spears is doing a lot better these days, with a successful residency in Las Vegas. Musically though, the “Oops I Did It Again” singer continues to tank. After splitting with JIVE Records, Britney Jean hit store shelves in 2013, and it sold only 107,000 copies in the United States in its first week. That’s Spears’ worst to date, and it didn’t do much better internationally.
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