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Britney Spears; 2007
So this was certainly a cringe-inducing comeback. That hair. That awful non-dancing (more like walking, really.) That belly-button ring. That desperation. Uh, and that song. That song is so bad. And the worst part? The next day, critics just kept calling her fat. Which, she is NOT fat. Low blow. Awkward. Let's all pretend this never happened.