The film stars Harrelson as an alcoholic ex-professional bowler who becomes the manager for a promising Amish talent played by Quaid. It was filmed in and around Pittsburgh, Pennsylvania (as a stand-in for Scranton), Amish country, and Reno, Nevada.
Flashy young bowler Roy Munson (Woody Harrelson) wins the 1979 Iowa state bowling championship and leaves home to turn professional. In his professional bowling tour debut, he defeats established pro Ernie McCracken (Bill Murray), who takes the loss poorly and seeks revenge. McCracken convinces Roy to join him in hustling a group of local amateur bowlers. When the amateurs become furious after realizing they are being conned, McCracken flees while Roy is brutally beaten and loses his hand when it is forced into the ball return, ending his career. Seventeen years later, Roy uses a prosthetic hand and is living in Scranton, Pennsylvania, where he sells novelty items with little success and drinks heavily. He is also behind on his rent and is constantly harassed by his landlady Mrs. Dumars (Lin Shaye), even going so far as to have sex with her to avoid her having him evicted and possibly prosecuted for staging a mugging with his friend in order for Roy to save her.
On a sales visit to a nearby bowling alley, Roy meets Ishmael Boorg (Randy Quaid). Roy tries to convince Ishmael to turn pro, with Roy acting as manager. Ishmael declines, explaining that he is from the local Amish community and that his bowling hobby is a secret. Roy then sees a poster in a bowling magazine advertising a $1 million winner-take-all tournament in Reno, Nevada. Learning that Ishmael's family is about to lose their farm to the bank, Roy eventually convinces Ishmael's family to let him join Roy.
Roy discovers that the childlike Ishmael is not aware of some of bowling's basic rules and skills, but after some coaching, Ishmael improves. The duo earn money in various local tournaments and by hustling bowlers. Ishmael defeats a wealthy bowling enthusiast named Stanley Osmanski (Rob Moran), but Stanley attacks the duo after discovering that the roll of cash Roy put up was fake. As the group flee Osmanski's mansion, his girlfriend Claudia (Vanessa Angel), who had also been a victim of Osmanski's violence, joins them. Roy suspects Claudia has ulterior motives and is distracting Ishmael. After Roy gets in a big fight with her, Ishmael flees. During his absence, Roy and Claudia drive on and end up at his family home, abandoned ever since Roy's father died years earlier, where Roy confesses he never went back for the funeral due to feeling ashamed for his failure as a pro bowler. They eventually find Ishmael and continue on to Reno.
In Reno, the group runs into McCracken, who is now a national bowling superstar. McCracken insults and makes fun of Roy and infuriates Ishmael, who attempts to punch McCracken but instead hits a wall and breaks his hand, leaving him unable to bowl. Later on, Claudia disappears with all of their money after being discovered by Stanley. Feeling distraught, Ishmael convinces Roy that they still have a chance to win the $1,000,000 – if Roy bowls. Roy enters the tournament, rolling the ball with his prosthetic rubber hand. He wins his first several rounds, ending up in the televised finals against McCracken. During the final match, Ishmael's brother, who had been sent by the Boorg family, arrives and takes Ishmael back to Pennsylvania. When Roy realizes he is alone, he struggles and McCracken wins the tournament by one pin.
Afterwards, Roy is again living in Pennsylvania when he is visited by Claudia, who explains she had disappeared with Stanley in Reno in an attempt to keep him from hurting Roy and Ishmael. She made Stanley believe she was running away with McCracken, and confesses her love for Roy, offering him money Stanley earned from gambling on McCracken in the finals. Roy responds that he has already earned $500,000 in an endorsement deal for Trojan condoms based on his prosthetic rubber hand. Roy and Claudia visit Ishmael's family home. Ishmael's parents explain that Roy and Claudia told them about Ishmael's forbidden bowling career, but also about the moral strength and decency he showed during his travels. Roy tells them how Ishmael straightened out Roy and Claudia's lives. Roy pays off the Boorg family's debts with his endorsement check, and Roy and Claudia drive away together.
Professional baseball pitcher Roger Clemens appears in a cameo as the character Skidmark during the restaurant scene. Professional bowlers Parker Bohn III, Randy Pedersen and Mark Roth appear as opponents that Roy Munson defeats on his way to the final match in Reno against McCracken.
The film also features several musical acts. Jonathan Richman (who would play an even bigger musical role in the Farrelly brothers' next film There's Something About Mary) fronts the band performing in the restaurant scene, while Urge Overkill performs the national anthem at the tournament in Reno. In the film's final scene Blues Traveler perform their song "But Anyway" while dressed in traditional Amish clothing.
Kingpin earned $25,023,434 at the box office.
The film initially received mixed reviews; Rotten Tomatoes currently gives the film a score of 50% based on 38 reviews, with an average rating of 5.8 out of 10. The consensus states: "Kingpin has its moments, but they're often offset by an eagerness to descend into vulgar mean-spiritedness."
However the film had some notable champions and has since commonly featured on cable television. Roger Ebert had one of the more noteworthy positive reviews, giving it 3.5 out of 4 stars. Gene Siskel also endorsed the film, putting it on his list of the ten best films for 1996.
Nancy Gerstman mentioned the film as one of the nine most underrated films in the 1990s.
The film is ranked #68 on Bravo's "100 Funniest Movies".
When released on DVD, Kingpin came in its original PG-13 theatrical version (113 minutes) and an extended, R-rated version (117 minutes). Both versions are available on the Blu-Ray disc issued by Paramount Pictures on October 14, 2014.
Lin Shaye attended a 1996 live airing of a Professional Bowlers Tour event in Wichita, Kansas, to both promote the film and present the winner (Jess Stayrook) with the winner's trophy and prize money. Stayrook defeated Butch Soper, who had won the first three matches.