Chasing Amy is a 1997 American romantic comedy film written and directed by Kevin Smith. The central tension revolves around sexuality, sexual history, and evolving friendships. It is the third film in Smith's View Askewniverse series.
The film contains explicit sexual dialogue and was originally inspired by a brief scene from an early movie by a friend of Smith's. In Guinevere Turner's Go Fish, one of the lesbian characters imagines her friends passing judgment on her for "selling out" by sleeping with a man. Kevin Smith was dating star Joey Lauren Adams at the time he was writing the script, which was also partly inspired by her.
The film won two awards at the 1998 Independent Spirit Awards (Best Screenplay for Smith and Best Supporting Actor for Jason Lee.)
Holden McNeil (Ben Affleck) and Banky Edwards (Jason Lee) are comic book artists and lifelong friends. Holden is the calmer, more reasonable of the duo; Banky, meanwhile, is the caustic and short-tempered half. Everything is going well for them until they meet Alyssa Jones (Joey Lauren Adams) at a comic book convention in New York where they are promoting their comic Bluntman and Chronic. Holden is attracted to Alyssa, but soon learns that she is attracted to women. The two begin hanging out, and a deep friendship develops. Eventually, Holden is no longer able to contain his feelings, and confesses his love to Alyssa. She is initially angry with him, but that night, the two begin a romantic relationship.
This new development worsens the tension between Holden and Banky, who dislikes and distrusts Alyssa and is bothered by her and Holden's relationship. Banky investigates and uncovers dirt on Alyssa's past, and he reports to Holden that Alyssa participated in a threesome with two guys during high school, which gave her the nickname "Finger Cuffs". Holden is deeply disturbed by this revelation, having previously believed that he is the first man Alyssa had ever slept with. He angrily confronts Alyssa while attending a hockey game, and clumsily attempts baiting her into confessing. During a tearful argument, she tells Holden about her "many" youthful sexual experimentations. She apologizes for letting him believe that he was the only man she had been with. However, she refuses to apologize for her past, and Holden leaves feeling angry and confused.
Later, during lunch with Jay and Silent Bob (Jason Mewes and Kevin Smith), Silent Bob reveals that he was once in a relationship similar to Holden's. Despite the fact that he was in love with his girlfriend, Amy, his insecurities about her adventurous sexual past caused him to sabotage the relationship and leave her. Angry at himself for letting her go, he has "spent every day since then chasing Amy, so to speak."
Inspired by Silent Bob's story, Holden devises a plan to fix both his relationship with Alyssa and his fractured friendship with Banky. He invites them both over and tells Alyssa that he would like to get over her past and remain her boyfriend. He also tells Banky that he realizes that Banky is in love with him—kissing him passionately to prove the point. Holden suggests a threesome. Though initially appalled, Banky agrees to participate, whereas Alyssa explains to Holden that it will not save their relationship. Before leaving, she states that she loves him, but she will not be his "whore." Banky also leaves the apartment, and summarily ends their friendship.
One year later, both Banky and Holden are busy promoting their own respective comics at a convention in New York. It is revealed that Holden has dissolved their partnership over Bluntman and Chronic, leaving the viewer with the assumption that he sold the publishing and creative rights over to Banky (which is corroborated in the beginning of Jay and Silent Bob Strike Back). Banky smiles sadly at seeing his old friend, who silently congratulates him for his success. Banky gestures over to a booth hosted by Alyssa, and provides wordless encouragement to Holden to go talk to her. He has a brief, quietly emotional conversation with Alyssa, and gives her a copy of Chasing Amy, his new comic based on their failed relationship. After Holden leaves, Alyssa's obviously new girl-friend (Virginia Smith) arrives and asks who she was talking to. A shaken, misty-eyed Alyssa feigns indifference and replies, "Oh, just some guy I knew."
- Ben Affleck as Holden McNeil
- Joey Lauren Adams as Alyssa Jones
- Jason Lee as Banky Edwards
- Dwight Ewell as Hooper X
- Jason Mewes as Jay
- Kevin Smith as Silent Bob
- Ethan Suplee as Fan
- Scott Mosier as Collector
- Casey Affleck as Little Kid
- Matt Damon as Shawn Oran
- Brian O'Halloran as Jim Hicks
- Carmen Llywelyn as Kim
- Guinevere Turner as Singer
- Joe Quesada (uncredited) as Himself
On a budget of $250,000, the film grossed a total of $12,021,272 in theaters. Chasing Amy played at three locations and earned $52,446 upon its opening weekend in the United States. The following week, the film was expanded to a further twenty-two theaters where it grossed $302,406. During the 18–20 April 1997 weekend, Chasing Amy was screened at a further 494 locations, where it earned $1,642,402 and moved into the Top 10.