I never found Letterman funny, and he comes off as mean and a little bigoted in this clip with the late, great Richard Simmons. But Simmons has a ton more charisma than Letterman, outshining him in a 4-minute clip produced by Letterman’s own team.

https://youtu.be/I4AflonZ6S4?si=QLkmjj6mHCNm1sE-
 https://youtu.be/I4AflonZ6S4?si=QLkmjj6mHCNm1sE- https://youtu.be/I4AflonZ6S4?si=QLkmjj6mHCNm1sE-