For many people, some of the best roasts date back to the Comedy Central Roasts that began in 2003. But for gut-busting comedy roasts, you cannot do better than the Dean Martin Celebrity Roasts.
This hilarious, long-running series ran for 10 seasons and began in 1974. Over the years, several high-end celebrities appeared on the show, including Evel Knievel, Betty White and Mr. T.
But one of the most well-remembered roasts was of the musical legend “Ol’ Blue Eyes,” Frank Sinatra. This episode had audiences around the country clutching their sides.
Dean Martin brought together a host of well-known personalities for the roast of Frank Sinatra. Among them were Milton Berle, Ernest Borgnine, George Burns, Red Buttons, Redd Foxx, Gene Kelly, Jack Klugman, Rich Little and Ronald Reagan.
While that list of people would have been enough to elevate this episode to one of the most popular, one of the comedians brought out all the stops for his roast.
That man was the inimitable comedic genius Jonathan Winters. For this performance, he pretended to be Frank Sinatra’s coach driver. He had the audience and the other roasters laughing as soon as he walked onstage.
If you know Jonathan Winters, it should come as no surprise that he stole the show. Watch this fully-improvised roast of Frank Sinatra. Nearly 45 years later, it still had us rolling on the floor.