Before watching the movie:
I have never heard of this movie before deciding to watch it. I’m not entirely sure how it fits the romantic comedy beats if they’re already together, but a comedy about art thieves getting in over their heads, with Sandra Bullock, sounds very appealing. I’m not sure if I’ve encountered Denis Leary in a romantic comedy role before, but that doesn’t detract from my interest. I’m really not sure about Leary starring in a romantic comedy he co-wrote though, which sounds like it could go very poorly.
Frank O’Brien, when hired by small time crime boss Beano Callahan to steal and sell a painting for a buyer on a New England island for ten grand, decides that instead of following instructions and stealing it on Sunday morning for sale on Sunday afternoon, he’ll steal it on Friday morning with his girlfriend Roz and they’ll make a weekend out of the trip to the island. Unfortunately, Frank is a really stupid crook, the police were already chasing them before they’re out of the state when their car broke down and they stole another one, and then when they left the stolen car to take the train, they left it at the station with Frank’s wallet in the seat. The theft of the painting, a priceless Matisse actually worth $4M, lands on the news, and Beano, already aggravated by Frank’s improvisation, decides to go steal it back himself and sell it for real money instead of the $500k the buyer told him it was worth. Arriving on the island, they break into a vacated house and pose to the art collector neighbor as friends of the owners making an unannounced stay while they’re away, a high-class kind of guy who offers Roz an alternative to seven unsatisfying years of arguments and stagnation with Frank. Following in the wake of the amateur thieves is FBI art theft expert O’Malley, who can’t believe how easy this case’s crooks are making it on him.
In this world of high-profile art theft, the central conflict in this movie is Frank and Roz’s dysfunctional relationship. And while it’s kind of fun when they’re just arguing, once they’re really on the rocks, it gets more frustrating than funny. Frank’s hapless efforts to try to win her back are just frustrating, I think because all of the best comedy comes from Roz’s end. When Roz is actually upset, it stops being fun.
At least everyone around them is funny. Yaphet Kotto plays the straight man to the dumbest criminals his character has ever seen. I was a little surprised to see Wayne Robson as a ruthless crime boss instead of a shy, ineffectual guy, but it turns out he’s an ineffectual crime boss. The local police in the town are the kind of lazy idiots they need to be to not find out about what’s going on under their noses, though they’d rather be running the video rental store that operates out of the sheriff’s office.
This is not the disaster it’s been made out to be, but it’s not as satisfying as it could have been. I’m not entirely sure that’s a failing of the direction and not a failing of the script, but I think it comes down a lot to Frank’s likeability. There are few people in this movie less likeable than the leading man, and that’s a major failure of an otherwise delightful little New England crime comedy.