Coin Toss (2013)

In the best screwball comedy tradition, This award winning film tells the story of love and luck turning on the toss of a coin. Tom Benett is trying to do the right thing, but his good intentions keep getting derailed by his scheming fiancé and a hustler who want his $350 million dollar lottery ticket. Mix in skulduggery with a stolen investment formula, a childhood sweetheart, and a couple of homicidal pensioners, and Tom has a long way to go before he learns that it's okay to lose once you've learned what's worth winning!

Unfortunately the movie Coin Toss is not yet available on HBO Max.