Never catching cases, why they faces look so e-m-o?

from Childish Gambino (Ft. Problem) – IV. sweatpants Lyrics on Rap Genius

Meaning

He’s steering clear of trouble, never getting caught doing a crime. Because he’s so driven, he’s outselling and outperforming lesser rappers, which makes them pout.

Emo is a style of music that tends to be with histrionic lyrics and melodrama. His success makes others cry.

Given all the sex in this verse, it’s likely he’s also referring to never catching an STD, though his love-‘em-and-leave-'em attitude does leave the girls sad.

Possibly an allusion two videos by the Mystery Team, who never actually solved a case: “The Case of the Haunted Hotel” were the governor avoided being caught with a high school girl and the “EMO Song”.

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