While appearing on the show Wednesday night, the actor gamely grabbed a mic and did a few verses of his hit "Gettin' Jiggy Wit It" with the help of the show's house band.
The impromptu performance of the 1998 hit (Yes, 1998. As in 17 years ago) delighted the audience and host David Letterman.
"That's so great -- I can't do that," he quipped.
Smith also brushed off his rap skills earlier this month, when he did "It Takes Two" with Jimmy Fallon on the "Tonight Show."
Watch below for a pretty perfect Throwback Thursday moment: