That you're going to be your nicest 'round your midlife crisis

from Lupe Fiasco (Ft. Ed Sheeran) – Old School Love Lyrics on Rap Genius

Meaning

Lots of rappers whose image is predicated on being “hard” tend to soften as they approach middle age. Compare Nas at 20:

https://www.youtube.com/watch?v=_srvHOu75vM

To Nas at 38:

https://www.youtube.com/watch?v=xP4_0z2M85Q

Alternatively, with “nicest” being used as a synonym for “best”, this could also mean that the new school rapper’s skills will peak when he’s older.

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