St. John of Las Vegas
(2010)

John (Steve Buscemi) is an unlucky compulsive gambler who drove his car as far as tank of gas would take him away from Las Vegas.  He ended up in New Mexico.  He was able to get a nice house in a gated community.  He was able to get his first cubicle desk job with an insurance company.  The best thing about it was his smiley-face obsessed cubicle neighbour, Jill (Sarah Silverman).  They are sweet on each other.

John meets with his boss, Mr. Townsend (Peter Dinklage) to get a raise.  Mr. Townsend sends him out with Virgil (Romany Malco) to do an insurance investigation.  If they can prove that this stripper is lying about her injuries and accident then John may get a promotion.

Various events for the investigation ensue:

Turns out Virgil, the stripper and the tow truck yard people are defrauding the insurance company for a LOT of money.  Virgil gives John $1000 to keep quiet.  John takes the money and spends $800 on lottery tickets.  He loses it all.

We see John back at the insurance company in an office.  Jill comes in.  They are boyfriend and girlfriend.  Jill left Mr. Townsend when John went off on his journey.  Virgil doesn't blackmail John with the phone photo of him and Jill in the women's handicap stall having sex right before he left on the investigation.

Jill comes in with a smiley-face scratch and win.  He could be the big winner and asks Jill if they win would she still love and stay with him after he blows all the money.  She says that technically she bought the ticket SO if they got married she could give him an allowance of the money.  He realizes then that when you don't need luck is when you are the luckiest.  Fade to black and you don't know if he wins or not.

Thanks Ann-Marie 'crappy' F!