Artists who accept commissions to paint portraits, no matter how esteemed they are in the realm of portraiture (or in fine art generally), learn to put their egos aside.

AROE, GREY, Matt Dosa, Feldman Sisters and Remi Rough all have roots in street art and have evolved into strong voices in contemporary art.

It’s past 1 a.m. on a Tuesday in downtown Manhattan, and A$AP Rocky, in a white long-sleeve tee and relaxed jeans—his khaki ...