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Frank Sinatra and Milton Berle played a hilarious prank on Jackie Gleason in the late '40s
His famous pals tried to teach Jackie a lesson
Practical jokes, when done properly, have the power to connect us all. At their harmless best, they're a great reminder not to take life too seriously. Pranks are an important part of having healthy humor; flexing that funny bone might just be the key to a long life.
One purported master of the practical joke was Jackie Gleason. Legend tells of the various pranks and jokes he'd play on other showbiz acts. However, in William J. Weatherby's 1992 biography Jackie Gleason, Gleason's friend Milton Berle recalled the details about a time Gleason was bested by his very famous peers. Gleason was building a reputation as an astute pool player, frequently making big money bets on himself.
Berle recalled, "[Gleason] was always sitting at Toots Shor's raving about his skill and praising himself as the world's greatest pocket billiard player. I remember I was there with Toots, Sinatra, Jimmy Cannon, the writer, and Gleason. Jackie was pouring it down pretty heavy. That is what he wanted to do, so let him do it. He was praising himself as usual, boasting, 'I can beat anybody in pocket pool.' Sinatra says, 'Anybody?' and Gleason says, 'Yeah, anybody.'
"In about an hour, a little guy showed up and Frank said, 'I want you to meet my tailor, Guido Lombardi.' The little guy had slick hair and looked the part. As we sat there, Sinatra says the little guy plays pool. Gleason was ready to play him and we said we'd bet. 'Yeah, pal. Anything you want to bet, pal,' Gleason said. If he forgot your name, he said 'pal.'
"Sinatra said, 'Let's go over to McGirrs' Billiard Academy at 6th and 50th, and you can play this little tailor.' Cannon, Shor, myself, and Sinatra each put up $100 that Gleason couldn't beat the man. He beat Guido the first four games, and we kept doubling the bets. Jackie was pretty good. We got to the fifth game with $7,400 in bets. Jackie was too cute in the fifth game; he broke up all the balls and said, 'Try to win some of your money back.' Guido proceeded to run 134 balls off consecutively."
But, this wasn't just a case of sudden good luck. It seems not everybody at the pool game was who they purported to be.
"He was really Willie Mosconi, the great champion. Jackie was mad when he knew: 'You brought this dark horse in on me.' Cannon said, 'It teaches you don't play cards with strangers.' He owed us $7,000, and he paid it off eventually, but it took a long time. We made him do it. We could have said, 'Forget it, it was a joke,' but we wanted to teach him a lesson."
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