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2. Lil Wayne

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“Why is Lil Wayne so lucky?” you might ask, when he’s been consistent with his career since he was 13 years old. While 'Tha Carter III' broke sales of one million in its first week, that was the gentle push Weezy needed to take his career to new heights. An 8-month prison stint in 2010, did nothing but secure his brand, thanks to the rise of Nicki Minaj and Drake. He even turned into a rockstar with his 'Rebirth' album, scared everyone with 'I Am Not a Human Being' and the best song on 'Tha Carter IV' -- the string of interludes -- didn’t even really feature him. So again, why is he so lucky? Isn’t it a little obvious?