Plot
As the opening credits roll, an armored truck brings money to load an ATM. A woman withdraws $20 but fails to put it in her pocket properly, and the bill slips away. It gets run over by a truck, while a homeless woman, Angeline (Linda Hunt), and several children independently chase after the bill. The woman grabs the bill and reads the serial number, proclaiming that it is her destiny to win the lottery with the numbers on the bill. As she holds the bill aloft in celebration, one of the boys grabs the bill from her on skateboard and uses it to buy an item at a bakery. The baker sells an expensive pair of figurines for a wedding cake to Jack Holiday (George Morfogen) for a few hundred dollars and gives him the bill as change. At the rehearsal dinner for the upcoming wedding of Sam Mastrewski (Brendan Fraser) to Anna Holiday (Sam Jenkins), Jack reminisces about exchanging his foreign money for American currency when he first came to America, and he presents Sam with the $20 bill as a wedding present. Sam is taken aback by the perceived cheapness of his father-in-law-to-be, but before he is able to say anything about it to anyone, he is "kidnapped" for his bachelor party. Sam uses the bill to pay the stripper (Melora Walters) at his bachelor party. Anna shows up at the party to explain that the $20 is not the entire present and to suggest that they should frame the bill to show that they understand its significance. Sam is unable to explain the absence of the bill, when the stripper comes in from the fire escape to offer it back to him. Anna apparently breaks the engagement.
The stripper uses the $20 bill to buy a herbal remedy from Mrs. McCormac (Gladys Knight). Mrs. McCormac mails the bill to her grandson Patrick (Willie Marlett) as a birthday present. Patrick goes to a convenience store where Frank (Steve Buscemi) and Jimmy (Christopher Lloyd) are engaged in a string of robberies. (During their spree, they keep Angeline from buying a lottery ticket at a liquor store.) Not knowing he's a robber, the underage Patrick gives Jimmy the $20 bill to buy him white wine. Jimmy goes into the store to find that Frank has botched the robbery. Jimmy and Frank leave, giving Patrick and his girlfriend Peggy champagne. The police chase the robbers, who pull into a deserted used car lot and blend in. After the police pass by, Jimmy and Frank split up the money, but when Frank sees the $20 Jimmy got from the kid, he assumes that Jimmy is holding out on him. Jimmy tries to explain but Frank pulls a shotgun on him. Jimmy shoots Frank and takes all the money they've stolen, but leaves the $20 bill. The bill, now dripped with Frank's blood, winds up in the police evidence locker but falls into the wrong box.
Waitress and aspiring writer Emily Adams (Elisabeth Shue) shows up at the police precinct with boyfriend Neil (David Schwimmer) to claim some items the police recovered. The policeman (William H. Macy) unwittingly includes the $20 bill. After flying out of the box from the back seat of Emily's convertible, the bill floats around town, and is picked up by a homeless man who uses it to buy groceries. (In this scene, Angeline is again unable to buy a lottery ticket.) The bill is given as change to a wealthy woman who uses it to snort cocaine off the back of her stretch limousine, although she leaves it on her car, where it is picked up by the drug dealer (Edward Blatchford).
The drug dealer also runs a day camp for youth, and he puts the bill into a fish where it is caught by a teen who has it converted to quarters and uses them to call a phone sex hotline in a bowling alley. The bowling alley owner (Ned Bellamy) gives the bill to his lover (Matt Frewer) and tells him to go out and have fun. The Frewer character encounters Sam, who is loitering in a daze behind the bowling alley. Sam turns down an offer of the $20 bill, not knowing it is the cause of his downfall. The Frewer character then uses it to play bingo at a church, where the priest is portrayed by Spaulding Gray. Emily's father, Bruce (Alan North) also plays bingo and receives the bill as change. When the Frewer character calls bingo, Bruce is apparently startled and dies of a heart attack.
At the mortuary, the mortician (Melora Walters), gives the family Bruce's personal effects, including his wallet with the $20 bill. Emily eventually looks in the wallet and finds the $20 bill in the wallet together with a copy of her first published short story. Her mother Ruth (Diane Baker) explains that Bruce also wanted to be a writer. Emily decides to go to Europe. At the airport, she explains her decision to her brother Gary (Kevin Kilner), and she melodramatically rips up the bill in front of him. (Gary was a witness to one of Jimmy & Frank's robberies.) Sam is also at the airport, waiting for a flight to Europe. Sam uses a piece of the ripped up bill as a bookmark but it falls out without his noticing it as Sam and Emily walk toward their gate. A title reading "The End" is derailed by Angeline collecting pieces of the bill.
Angeline sits down at a coin-operated TV and patches the bill back together. Just then the lottery numbers are read, and to her agony, they match the serial number of the bill. She goes to a bank and inquires if the bill is still any good. The teller explains that if there's more than 51% of the bill left, it is still valid, and hands Angeline a crisp new $20 bill. The homeless woman dramatically reads the serial number of the new bill and leaves the bank.
A running gag in the film is Emily, a writer, being unable to find her pen.
Read more about this topic: Twenty Bucks
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