Obediah "Sky" Masterson is one of the four main characters of Guys and Dolls. He is known as one of the greatest gamblers in the country; he takes wild bets and surprisingly ends up winning big. When taking a bet from old friend, Nathan Detroit, the plot intiates as he tries to sweep Miss Sarah off her feet and take her to Havana.
Guys and Dolls (Musical)Sky makes his first appearance after Nathan Detroit ditches off Miss Adelaide to his assistants, Benny Southstreet and Nicely-Nicley Johnsosn. He states that he had just returned from Nevada with his winnings of $50,000. Sky also plans to go to Havana, where there is a lot of action. He invites Nathan, he declines. Nathan, scheming to get $1,000 off of Sky for the crap game he runs, offers to bet that Mindy's Restaurant selled more strudel than cheesecake. Sky, being his smart and clever self, realizes Nathan's plan. He tells Nathan the advice Sky's father gave him before "Went out in the world." After the story, Sky bets Nathan the same thousand that Nathan does not know the color of neck tie he has on (Sky covers Nathan's ties). Nathan gives up and they then begin talking about why Sky does not have a doll with him to take to Havana. Sky believes that "figuring weight for age, all dolls are the same." and that he doesn't take a doll because he likes to "travel light."
sky masterson is a cunt mate