1. Failing to complete more than 500 hours of court-ordered community service in 2008
This didn't have a lot to do with his actual career, but it did end up affecting it in a major way. In 2008, when Gucci Mane's star was just starting to shine brightly, he violated the probation he received after getting arrested in 2005 for aggravated assault by completing just 25 of the 600 court-ordered community service hours that were given to him. As a result, he was sentenced to a year in a country jail and ended up serving six months in 2010. It completely killed all the momentum he had going at that time.
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