Dennis know the game, he in the crowd mackin
Macking-to attempt attracting a member of the opposite sex.
Cudi is implying that his friend Dennis is a master pick up artist, by mentioning that he know’s the game.
This can also be a reference to It’s Always Sunny in Philadelphia. He has no other reason to mention Dennis as the character that is “Mack"in —– Or it could be a reference to Mac and Dennis.
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