Sky Masterson - The Man Behind the Dice

This summer I'll be performing the iconic role of Sky Masterson in Guys and Dolls. This role has been performed by such iconic actors as Marlon Brando, Robert Alda, Peter Gallagher, Ron Raines, Ewan McGregor, Craig Bierko, Brian Stokes Mitchell, and Patrick Wilson.

Sky Masterson was a character first crafted in a short story by Damon Runyon - "The Idyll of Miss Sarah Brown." Runyon describes Sky Masterson like this...

“Of all the high players this country ever sees, there is no doubt but that the guy they call The Sky is the highest. In fact, the reason he is called The Sky is because he goes so high when it comes to betting on any proposition whatever. He will bet all he has, and nobody can bet any more than this.

His right name is Obadiah Masterson, and he is originally out of a little town in southern Colorado where he learns to shoot craps, and play cards, and one thing and another, and where his old man is a very well-known citizen, and something of a sport himself.

He is maybe thirty years old, and is a tall guy with a round kisser, and big blue eyes, and he always looks as innocent as a little baby. But The Sky is by no means as innocent as he looks. In fact, The Sky is smarter than three Philadelphia lawyers, which makes him very smart, indeed, and he is well established as a high player in New Orleans, and Chicago, and Los Angeles, and wherever else there is any action in the way of card-playing, or crap-shooting, or horse-racing, or betting on the baseball games, for The Sky is always moving around the country following the action."


The REAL Sky Masterson, a Man Named Titanic

Damon Runyon based The Sky off of the infamous gambler Titanic Thompson. Thomas was born in southwestern Missouri but raised mainly on a farm in the Ozark Mountains. Thomas spent most of his youth developing skills he would use later, such as shooting and understanding odds at card games through marathon dealing of hands.

Alvin Clarence Thomas AKA Titanic Thompson -

"In the spring of 1912 I went to Joplin, Missouri, just about the time the Titanic liner hit an iceberg and sank with more than 1,500 people on board. I was in a pool room there and beat a fellow named Snow Clark out of $500. To give him a chance to get even, I bet $200 I could jump across his pool table without touching it. If you think that’s easy, try it. But I could jump farther than a herd of bullfrogs in those days. I put down an old mattress on the other side of the table. Then I took a run and dived headfirst across the pool table. While I was counting my money, somebody asked Clark what my name was "It must be Titanic," said Clark. "He sinks everybody." so I was Titanic from then on."

When he had honed his skills, he became a "road gambler", a traveling hustler who became an underground legend by winning at all manner of propositions, many of them tricky if not outright fraudulent. Among his favorites were: betting he could throw a Walnut over a building (he had weighted the hollowed shell with lead beforehand), throwing a large room key into its lock, and moving a road mileage sign before betting that the listed distance to the town was in error. He once bet that he could drive a golf ball 500 yards, using a hickory-shafted club, at a time when an expert player's drive was just over 200 yards. He won by waiting until winter and driving the ball onto a frozen lake, where it bounced past the required distance on the ice.

Blessed with extraordinary eyesight and hand-eye coordination, he was a skilled athlete, crack shot and self-taught golfer good enough to turn professional. In an era when the top pro golfers would be fortunate to make $30,000 a year, Thompson could make that much in a week hustling rich country club players. Asked whether he would ever turn professional, he replied, "I could not afford the cut in pay". He can play right- or left-handed. One hustle of his was to beat a golfer playing right-handed, and then offer double or nothing to play the course again left-handed as an apparent concession. One thing his opponent usually did not know was that Thomas was naturally left-handed. Thomas' genius was in figuring out the odds on almost any proposition and heavily betting that way. He also had to perform under pressure, and most often did.


Until Next Time,

Lift Big, Sing Big, and Look Your Absolute Best Doing It

Kasey (Ol') Yeargain