Grab a cup of that XO, baby I been leaning

from The Weeknd – Initiation Lyrics on Rap Genius

Could be too things:

XO as in XO Hennesey, in this case XO would stand for “Extra Old”.

XO is also a term The Weeknd came up for lean. He drinks XO so much he made his crew name on that. Also Drake is big on lean now and constantly mentions XO because of his affiliation.

Make’s sense since he’s “leaning”

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