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The unluckiest man in Vegas - a guy whose bad luck is contagious - is used by the last of the old time mob run casinos to kill high rollers action. That is, until he falls in love with a cocktail waitress and gets "lady luck," which throws the situation into reverse. Things turn nasty when the casino director tries to break up the romance.
The Shangri-La Hotel and Casino in Las Vegas is managed by Shelly Kaplow, who hates what has been the Disneyfication of the Strip as he is "old school Vegas", still doing things the old fashioned way catering to who he considers old fashioned clients, i.e. those who remember and admire people like the Rat Pack. One of those old fashioned measures is to use threats, intimidation and violence, implied or real, to deal with players trying to scam the casino. Another old fashioned measure he has implemented is to employ Bernie Lootz as a "cooler": turn the winning fortunes of casino players into losing ones. Bernie is a sad sack, a schmuck and a loser, so he does his job, and does it well, by hanging around those players with hot streaks and just being himself. Bernie could not turn down Shellys offer of employment as he owes Shelly money, Shelly who broke Bernies knee for that debt, with the result being that Bernie still walks with a limp. Bernie will be able to pay Shelly off with one more week of employment, after which he is determined to leave Vegas forever, putting this miserable phase of his life behind him. Things change for Bernie on two fronts. First, his estranged grown son Mikey and his very pregnant girlfriend Charlene enter his life, they who need money for the baby and who will get it any way they can. And second, Bernie is attracted to Natalie Belisario, a new waitress at the casino, who seems to be equally as attracted to him. Natalie, who believes in the alignment of the stars affecting ones life, only sees them in a relationship if they stay in Vegas. As such, Bernie has to decide if Natalie in his life is worth remaining in Vegas. Things may also be changing for Shelly as Nicky Bonnatto, one of his mob investors, has brought in a young Harvard grad named Larry Sokolov as an advisor to modernize the operation. Shelly may try to protect his way of life, against Nicky, Larry and others, in the only ways he knows how.
William H. Macy
Bernie Lootz
Maria Bello
Natalie Belisario
Alec Baldwin
Shelly Kaplow
Shawn Hatosy
Mikey
Ron Livingston
Larry Sokolov
Paul Sorvino
Buddy Stafford
Estella Warren
Charlene
Arthur J. Nascarella
Nicky Fingers Bonnatto
Joey Fatone
Johnny Cappella
M.C. Gainey
Highway Officer
Ellen Greene
Doris
Don Scribner
Lou
Tony Longo
Tony
Richard Israel
Marty Goldfarb
Timothy Landfield
The Player
T.J. Gioia
Bulldog
Jewel Shepard
Hooker
Gordon Michaels
Mr. Pinkerton
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