Kingpin begins with Woody Harrelson as Roy Munson, a child bowling prodigy who won the 1979 Iowa state amateur championship. Young Roy is all set to leave his tiny hometown of Ocelot, Iowa to go on the professional bowling tour. He wins his first tournament, defeating a none-too-pleased established pro named Ernie McCracken (Bill Murray) in the finals. Roy receives an oversized check and the enmity of McCracken.
The unhappy McCracken decides to get back at the young bowler, first by putting sugar in his gas tank, then convincing him to join him in a bowling-alley hustle. Munson needs money to repair his car engine, so he agrees. The scheme goes horribly awry when their "marks" realize they've been hustled. Roy is abandoned by the opportunistic McCracken and the angered marks shove Roy's right hand into a ball-return, amputating it.
In the present, a down-and-out Munson, sporting a hook which he covers with a fake rubber hand, sells bowling alley supplies with little success. He lives in a seedy apartment building in Scranton, Pennsylvania along with several winos and a landlady who is constantly after Roy because he never pays his rent on time.
On a sales call, Munson catches sight of Ishmael Boorg (Randy Quaid) rolling a respectable game. Munson tries to get him to turn pro, since he claims to have a "265 or 270" average. The Amish man has little interest in worldly affairs, though. He isn't even supposed to be bowling, as it is against Amish tradition, and he reluctantly admits it is the only "vice" he and his grandfather enjoy.
Munson's troubles increase after he tries to scam his elderly landlady into a rent extension. In the end he has to pay in kind -- with sex. While puking in a toilet after prostituting himself, Roy sees a headline on a bowling magazine that alerts him to a $1,000,000 winner-take-all purse in a tournament in Reno, Nevada. Roy decides to head out to Amish country posing as an Amish man from Ohio named "Hezekiah" Munson and visiting the Boorg family home to convince Ishmael to enter the tournament, where they'd split the winnings evenly. Ishmael again refuses, but soon receives news from his father that the family will lose their land unless $500,000 can be raised soon. The faithful Amish man reluctantly agrees to go along (which at the same times somewhat serves as Ishmael's rumspringa period), only to earn enough to save his people.
It quickly becomes apparent that Ishmael isn't as awesome as his "270" average would indicate. He explains that the average is based on a 15-frame game (instead of the standard 10 frames), since the Amish are obligated by tradition to do everything "half-again" as much as everyone else. Roy decides to take Ishmael home, because he no longer believes he can win the $1,000,000. Ishmael convinces Roy to take him to Reno, saying he didn't want to be "Munsoned" out in the middle of nowhere (meaning up the creek without a paddle, much like Roy).
After a little coaching and cajoling (and with Roy serving as a devil's advocate to Ishmael by getting him to smoke, drink coffee, and later on in the movie getting two tattoo's & drinking flaming whiskey) Roy convinces Ishmael to bowl for money. Both end up at gangster Stanley's house in the middle of the night to bowl a cash match on Stanley's private pair of lanes. Stanley resorts to using his girlfriend Claudia (Vanessa Angel) as a teasing distraction. It does not work, as Ishmael is incorruptible. After Ishamel wins, Stanley sees Roy handling a roll of fake money. Stanley realizes that the two were betting with money they never had. Luckily, they are able to escape (the luscious Claudia leading the way), and continue their journey towards Reno, with Ishmael's bowling skills and Claudia's ability to distract male bowlers gaining them a significant cash "stash."
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