I'm never the winner, always the loser

from Tyler The Creator (Ft. Hodgy Beats) – Slow It Down Lyrics on Rap Genius

Meaning

Tyler has claimed that he wasn’t all that popular in school…

This line and the next suggests that Tyler doesn’t attempt to win like other rappers do (by having the “freshest clothes” or the “flyest whips”), except for the fact that he loves bitches (“but i will choose her”).

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