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It involves small-time mobster Larry Gigli (played by Affleck; pronounced "zheely") being commanded to kidnap Brian (Justin Bartha), the mentally-retarded, Baywatch-obsessed brother of a district attorney trying to bring down a mob lord and hold him hostage. However, his boss doesn't think he'll be able to handle him by himself, so he has assassin Ricki (Lopez) join him. Gigli is attracted to Ricki, but she initially rebuffs him due to being a lesbian. Much of the remaining film time comprises the three hanging around Gigli's apartment, receiving threatening phone calls and break-ins from Gigli's boss and the police, and occasionally venturing to locales such as an outdoor diner and hospital, with strong emphasis placed on the romance between Ricki and Gigli and some rather strange lines.
Originally written strictly as a black comedy, it was rewritten to cash in on the Affleck/Lopez romance (then a major media craze) at the behest of executives. This turned out to be a colossal mistake, as the media saturation of "Bennifer" combined with the film's already dubious quality led to audiences growing sick of the film before it even opened. When it did open, it was to overwhelmingly negative reviews and a massive commercial failure. The movie is notorious for being so sorely lambasted that it's name is synonymous with terrible films in the public consciousness. To cap it off, it was the first film in the history of the Razzie Awards to pull a "Razzie Grand Slam" for Worst Picture, Actor, Actress, Director, and Screenplay (as well as "Worst Screen Couple"). It even picked up another award the following year for "Worst Comedy of Our 25 Years".
- Bloody Hilarious: This loving close-up of the fish in the aquarium eating pieces of Louis' brain.
- Boom! Headshot!: Al Pacino's scene has him doing this to a mob boss.
- Cluster F-Bomb
- Cure Your Gays: Ben Affleck is either a cure for lesbianism or an exception.
- Gayngster: Ricki; a female Gayngster, for a change.
- Lipstick Lesbian: Ricki.
- No Bisexuals: Ricki is a "lesbian" who has been with men (and does not state it was unpleasant, or a mistake,) and falls for Ben Affleck.
- Magic Bullets: Either this, or that was an extremely sturdy aquarium behind the bad guy when he gets shot.
- Misplaced Names Poster: Since when is Ben Affleck a girl or Jennifer Lopez a guy?
- Mood Whiplash: The film's tone changes numerous times at the drop of a hat, perhaps most noticably with a lighthearted scene with one of Ricki's ex-girlfriends...who slits her wrists in front of her and Larry after a couple minutes.
- Never Trust a Trailer
- Psycho Lesbian: Ricki's ex-girlfriend Robin. She turns up at Gigli's door, demands Ricki take her back and when she refuses, she slits her wrists.
- Running Gag: They all think his name is pronounced "giggly".
- Soundtrack Dissonance: A lengthy reflection on human sexuality by Jenny in which she compares the penis to a sea slug and the vagina to a human mouth is accompanied by a soft, mellow, romantic guitar ballad.
- There's also Ricki giving a speech about killing off the hostage, while a lighthearted folk guitar plays in the background.
- Tourettes Shitcock Syndrome: Brian.