Born Cassius Clay before converting to Islam, Muhammad Ali would refer to himself as “the greatest” and he certainly worked hard to back that up. Olympic gold medalist, multiple time boxing champion, and once fought a depowered Superman in the comics, Ali could be controversial but it takes a lot of guts to say something bad about him to his face.
Or appear on Dean Martin’s Celebrity Roast.
Born Dino Crocetti before converting to Hollywood, Dean Martin was a well known actor both with fellow comedian Jerry Lewis and as a member of Frank Sinatra’s “Rat Pack”. His comedic persona was a hard-drinking playboy, though that wasn’t quite accurate to his actual persona. The Dean Martin Celebrity Roasts were a series of specials in which Martin would roast a celebrity alongside other celebrities, often friends of the guest of honor.
Surprisingly, Martin along with co-roasters Red Buttons, Foster Brooks, Ruth Buzzi, Charlie Callas, Wilt Chamberlain, Howard Cosell, Billy Crystal, Georgia Engel, Rocky Graziano, Sherman Hemsley, Gabe Kaplan, Gene Kelly, Tony Orlando, Floyd Patterson, Freddie Prinze, Nipsey Russell, Isabel Sanford and Orson Welles (copy/pasted the list from Wikipedia) managed to survive the experience because this was back when people didn’t take themselves so seriously they couldn’t have fun with some mild ribbing. Enjoy.
If you want to see more of these roasts and the celebrities that took part, the shows are up on Shout Factory TV and the Shout Factory app.