31 thoughts on “Don Rickles roasts Clint Eastwood behind the scenes of Kelly’s Heroes

  1. Don Rickles riffing like this still holds up today, even if we are unaware of who he is talking about. Watching Clint Eastwood laugh like that was so funny and out of character for him at that time in his career. Watched Kelly’s Heroes again last night so enjoyed this clip even more.

  2. Saw this movie last night on an antenna station called movies lastnight. Such a classic and I love me some oddball.

  3. Classic Rickles comedy! He was a genius at insult comedy. The roasts he would do with Dean Martin and others was comedy gold! Actual humor not like the ones today you see on comedy central.

  4. There really isn’t a Sinatra like character today, so it’s hard to draw parallels, but he was big. When he came to town in his prime, he was the only game in town big…he could pack a room, a concert hall or a theater.

    He had a long time collaboration with Don Rickles, and the two became friends. They grew so close that Rickles became one of the only people who could make fun of Sinatra and get away with it…Sinatra was known for many things, a self deprecating humor wasn’t one of them.

    Rickles is on a date one night and spots Sinatra across the room. He excuses himself for a minute and sneaks over to Sinatra’s table. “Hey, Frank” he says “I’m with this girl, and you could really help me out by just coming over and saying hi.”

    “Alright,” Sinatra says “let me finish my espresso and I’ll swing over on my way out.” Rickles goes back to his date and as promised a few minutes later Sinatra he goes over to say hi. “How ya doin’ Don?”

    Rickles looks up from his plate and says “Geeze Frank, can’t you see I’m eating?”

    Gobsmacked, Sinatra walks out of the restaurant.

    Rickles had stones.

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