Blue City
From Wikipedia:
Returning to the small Florida town where he grew up, Billy Turner learns that his father has been killed. With little help from the police, Billy will take matters into his own hands and go up against a ruthless local mob in a desperate search to find the killer.
The film was considered a disappointment by critics upon release.[14][15]

Nelson's performance was particularly criticized, USA Today saying "Is Judd Nelson the smirkiest actor in current movies, or is he simply getting stereotyped playing overbearing creeps? Either way, you spend `Blue City's' 83 interminable minutes begging to deck him." The LA Daily News said "You haven't seen anything quite so ridiculous as a limp-jawed, dewy-eyed Nelson trying to carry off a tough guy part." "Nelson-.008 charisma rating on the Richter scale-is resolutely unconvincing." (L.A. Herald-Examimer). "It's another step in the slow process of revealing, movie by movie, what dull actors some of the celebrated Brat Pack kids are. Judd Nelson would make a great shopping cart, Sheedy a still life of a cornflower gone to wilt." (San Francisco Chronicle) "(The main character has) a passion as rootless as an Everglades air plant. . . . Though his clothes suggest that he and Don Johnson patronize the same boutique, Mr. Nelson has the looks of someone who's come South on a spring break and overshot Fort Lauderdale." (The New York Times) "The worst major studio film we've seen in recent memory." (Santa Monica Outlook) " Blue City is fictionally set in Florida, but was lensed entirely in California, thus managing to shame the citizenry on one coast and the film making industry on the other, all at the same time." (Daily Variety)[13]

Why it should be riffed:
1. Ally Sheedy and Judd Nelson actually have chemistry
2. However, you root for the bad guys throughout the movie
3. David Caruso is Ally Sheedy's brother in the film. No, really.