Here he is using the pun “Littlest” to refer to rappers who put the word “Lil” in front of their names. He is saying that he was a nobody at 16, just like a lot of the rappers like Lil B and etc at that age. #Based
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Sometimes he struggles a lot with the music industry and the direction he is heading in his music career and sometimes wonders what it would be like to sell your soul for money and fame.
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Here he is expressing his anger and hatred towards her after he saw her with the other guy at a Diner, and if he couldn’t control himself as well as he did, the altercation could have turned ugly.
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Before he went overseas he had a long talk with his girlfriend about not keeping secrets and etc. which she broke when he got back and she was caught sleeping around.
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Here he is referring to the time when he spent $300 on prostitutes in Amsterdam while still having a girlfriend back home which he felt somewhat regretful about it.
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