Watch Jimmy Kimmel Embarrass Jay Z With an Old Rap Video

It’s fitting that Brooklyn-born rapper Jay Z was reminded of his past on Tuesday’s episode of Jimmy Kimmel Live!, given that host Jimmy Kimmel has been broadcasting all week from the Brooklyn Academy of Music. Unfortunately for Jay Z, the sentimental trip down memory lane got a little embarrassing for him.

Kimmel unveiled a clip of a much younger Jay Z rapping alongside contemporary Big Daddy Kane. While the host called the clip “amazing,” Jay Z was more uncomfortable than anything.

“That was embarrassing,” the rapper said. “The haircut, the shirt—”

Kimmel did agree the fashion might be slightly dated: “It looked like you’re going to play a round of golf after.”

Watch the clip below to see a young Jay Z embarrass an older Jay Z.

This article originally appeared on EW.com