The best thing that can be said about 8 Heads is that it is wildly unpredictable, but that's only because every artistic decision by writer/director Tom Schulman defies explanation. The premise is pretty simple: Aging gangster Tommy (Joe Pesci) has been given a duffel bag filled with the decapitated heads of eight mobsters, with instructions to drop them off in San Diego within 24 hours. Tommy knows how to play the airport security, but once he's on the plane, his attitude prompts a stewardess to insist on putting his bag in cargo. As the hacky joke goes, Tommy's bag ends up with Charlie (Andy Comeau) instead, off to Mexico for a weekend vacation with his girlfriend Laurie (Kristy Swanson) and her parents, Dick (George Hamilton) and Annette (Dyan Cannon).
The natural assumption is that Charlie will discover the bag mix-up, and spend the weekend trying to prevent Laurie and her parents from discovering his gruesome problem without ending his relationship. Instead, Schulman has Charlie comically expose the heads at pretty much every opportunity. Not every character catches on (Dick sees the bagged skulls and assumes it's sacks of laundry), but this is the kind of thinking that sets up running jokes, such as the one where Annette finds the heads and thinks Charlie is a serial killer, falling out of sobriety and back into alcoholism and drug abuse as she endures what amounts to several days of gaslighting. At one point, Laurie even knocks her unconscious instead of explaining the situation. Other jokes include Charlie's fear of the police in "a third-world country," a roving band of thieves that steal Dick's car twice while in Charlie's possession, and the loss of multiple heads to various mishaps and mistakes.
Another assumption one might make is that Charlie and Tommy would spend more time in the same place during the movie, while Tommy tries to retrieve his precious cargo. Instead, Tommy discovers an unpublished novel in Charlie's luggage and heads to his medical school instead, where he spends most of the movie torturing Charlie's friends Ernie (David Spade) and Steve (Todd Louiso). While many viewers might delight in the idea of David Spade being tortured, their extended antics just feel like wheel-spinning preventing Tommy from finding Charlie and getting the movie over with. Their whole story is also oddly dull, despite the thread introducing a cryogenic laboratory full of other decapitated heads, and the removal of further heads from medical cadavers, in an attempt to replace some of the heads that are missing with convincing duplicates.
At the center of this maelstrom of bad decisions, two culprits stand the tallest: Schulman's screenplay, and the casting of Comeau as Charlie. Schulman never truly settles on whether or not he wants the movie to be a black comedy or a broad, near slapstick affair, styles which feel instinctively incongruous with one another (although it does lead to the movie's most memorable sequence, featuring the heads, all impressive creations by Greg Cannom, singing a parody of "Mr. Sandman"). This is problem enough through the first 75 minutes of the movie, but worsens as Schulman suddenly decides to try and humanize a mobster who has been presented consistently as an asshole who doesn't really seem to have any resistance to murdering innocent people, even if he never does (the film conveniently retcons one straight-up killing during the end credits). There's no reason at all for the audience to root for Tommy's success, much less for poor Charlie to help him, but Schulman confidently guides the film in that direction in the final 20 minutes. Meanwhile, despite having nothing to work with, Comeau's lack of knack for comedy or drama still creates a void at the center of the movie. Looking at him and the style of performance he delivers, it's clear that Schulman thought Comeau was either the next Tom Hanks or the next John Cusack, but he doesn't have the talent to live up to that lofty goal.
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