The last real Talk Show late night hosts were Johnny Carson and Jay Leno, but Carson was the best of all of them.
During the Clinton Monica scandal Leno made frequent jokes about it and was asked if he was anti Clinton. He said in effect, his job is to entertain his audience and the jokes wrote themselves with Clinton.
Leno did it in a way that it was funny and it wasn't really political. Mostly it was related to Lewinsky and he left it at that.