Off everything my pen wrote we went from Bundy to Winslow

from Drake – Tuscan Leather Lyrics on Rap Genius

Meaning

On the strengths of his raps, Drake went from the working class income of the Bundy family—of the sitcom, Married… with Children—to the upper middle class life of the Winslow family—of Family Matters. Both families are from Chicago.

The Winslows balled pretty hard.

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