27. Aaron Carter

When the Backstreet Boys were the biggest boy band in the world, there was nothing they couldn't do. To demonstrate that fact, Backstreet Boy Nick Carter pulled all the strings he could to make his less-talented younger brother Aaron Carter famous. For a brief time, it worked; 'I Want Candy' and 'Crush on You' were popular with the young teen market, and Carter must have thought that he was set for life. He wasn't.

Carter's problems started when - surprise, surprise - he failed to pay his taxes. As we now know, nobody gets away with that for long, so when the IRS caught up with him, they took him for all he had. His biggest payday since was an appearance on 'Dancing with The Stars,' but we don't think we'll ever see a hit song from him again.

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