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Film / Win It All

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Win It All is a Romantic Comedy Netflix original film. Starring Jake Johnson as Eddie, it follows him as he tries to pull himself up out of a gambling debt he's racked up so that he can keep the relationship with his girlfriend, Eva (Aislinn Derbez), alive.

Also features a minor role with Keegan-Michael Key playing Gene, Eddie's sponsor at a gambling addiction group.

This film contains examples of:

  • Disappeared Dad:
    • Eddie and Ron's father died before the movie's start.
    • The father of Eva's daughter ran off on them.
  • Food End: The film ends with Eddie making it to dinner with Eva's family.
  • Foolish Sibling, Responsible Sibling: Eddie is an on-and-off recovering gambling addict who is often losing a substantial amount of money; Ron is the boss of his company while also a devoted Family Man.
  • Gambler's Fallacy: Invoked multiple times by Eddie, frequently claiming that he's on a "streak".
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  • The Gambling Addict: The film's main focus is Eddie, a gambling addict, trying to clear his debts.
  • Happily Ever After: Eddie is able to pay off his debts and gets the girl.
  • Here We Go Again!: Eddie is so heavily addicted to gambling that even his sponsor is setting him up with games by the end of the movie. He hasn't changed at all and will almost certainly end up in debt again.
  • Hollywood Heart Attack: Subverted. Eddie suffers a heart attack. It's long and drawn out, and he doesn't even realize it's happening for over a minute.
  • Hospital Hottie: Eva is an attractive nurse employee.
  • Meaningful Name: Ron and Eddie's father was nicknamed "Chips" because he would always yell for them when out gambling.
  • Missing Mom: Ron and Eddie mention their father but their mother is never spoken of.
  • Multigenerational Household: Eva lives with her daughter and mother.
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  • Off the Wagon: For six weeks, Eddie is clear of gambling, has a steady job, and seems to be recovering. Then the person who he owes money to calls and informs him he's going to be collecting much earlier than expected.
  • Papa Wolf: After losing roughly $50,000 from the gambling game Gene sent him to, Eddie was about to run away until he got a message from Eva's daughter, he goes right back in to win back the money.
  • Professional Gambler: Eddie, prior to the film, refuses to get a real job and instead lives doing odd jobs and gambling it all.
  • Race Against the Clock: Eddie needs to get back the money he lost within six months. His time frame is later reduced to eight days.
  • Spicy Latina: Downplayed. Eva is an attractive woman of Hispanic descent but doesn't dress in anything too provocative.
  • The Sponsor: Gene.
  • Trapped by Gambling Debts: The film's plot. Eddie uses money that isn't his to gamble and ends up way deeper in debt.
  • Tropaholics Anonymous: Eddie attends a gambling addiction group.

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