Jay Z Gets Embarrassed by Old Rapping Clip: See His Funny Reaction!

What would Bey think? Tuesday, Oct. 20, was a big night for Jay Z. The Brooklyn, N.Y. native returned home to throw a blowout concert at Barclays Center in support of his music streaming service, Tidal. But first he appeared on Jimmy Kimmel Live!, where fans got a taste of HOVA’s rap history. 

When host Kimmel asked the rapper to recall his first-ever show, Jay, 45, replied, “I forgot the lyrics. The worst show ever.”

Jay Z and Jimmy Kimmel
Jay Z talks to Jimmy Kimmel about his first rap show.

Sadly, there was no footage from this event, but Kimmel did unearth a throwback clip of his first television performance with Big Daddy Kane

The segment, which looks like it comes from the early ‘90s, features a very young Jay Z wearing a striped red and white polo shirt with a high top fade haircut. 

Jay Z
Jay Z raps in his first televised performance in the early '90s.

“Here I am, the man. I’m swinging and singing and bringing the mic, again,” Jay speedily raps through his freestyle. 

“That was embarrassing,” the Grammy winner told Kimmel after the clip aired. “The haircut, the shirt, I mean.”

Later in the evening, Jay took the stage at Barclays Center, performing “Holy Grail” with his wife, Beyonce, and closing the show with his hit “Empire State of Mind.” 

Watch the video now to see his funny reaction! 

Sign up now for the Us Weekly newsletter to get breaking celebrity news, hot pics and more delivered straight to your inbox!

Want stories like these delivered straight to your phone? Download the Us Weekly iPhone app now!

Close popup

Welcome to In Motion

Bring photos to life with Us Weekly's exciting new mobile experience!

What's In Motion? Tell me more

What's In Motion?

Go back

How to Use In Motion

What's In Motion? Tell me more