Michelle Wolf reminds me a little of Joan Rivers in the 1950s and 1960s

They both have a very east coast caustic style of humor that is extremely cynical but also funny beyond belief at the same time. I find listening to her very "Freeing" in some ways and other times "like most good humor" I find myself wincing a little as it pushes boundaries I didn't know needed to be pushed.

But, that is what all Good comedians do. Joan Rivers and PHillis Diller were two of the female breakthough comedians in the 1950s and 1960s with a very tough skin like Michelle Wolf.