Remember I used to do things that'd make you laugh
Like orderin' a girl drink in a masculine glass
A neat microcosm of Kanye’s general appeal right here: his ability to constantly make fresh, unusual musical combinations and to wrap it all up in a unique sense of humour (nowadays employed alongside other various luxuriant packagings).
In this case: Yeezy gets a traditionally “girly” drink, perhaps an Appletini, put into the manliest package possible. Very similar to this scene in Scrubs:
At the same time, you could see this as kind of reminiscent of “All Falls Down”: Kanye doesn’t want to be seen holding a womens' drink, but at the same time he’s very honest about his insecurity and the front he puts up.
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