Screwed (2000)

Norm MacDonald is sick of his wealthy, ungrateful boss, and enlists his buddy (played by Dave Chappelle) to help kidnap and ransom her dog. Because they're morons, the dog escapes immediately, and all the evidence they left behind makes it appear it was MacDonald that was abducted. So they pivot into that, figuring they can still get the ransom money, fake his death with the help or a coroner played by Danny DeVito, and flee to another country.

Except, again, they're morons, so this doesn't work at all. The lead cop is smart enough to know something is off about this whole thing, but dumb enough it takes him most of the movie to figure out what's going on.

It's a hit-or-miss movie. The hook is good. Miss Crock owns her own bakery company, wealthy enough to hand out 50 grand to someone as a Christmas gift, but begrudges Norm's request for a new work suit after 15 years. Treats his request like it's selfish or unreasonable, as though he should be grateful for the opportunity to do everything for her around the house for minimal pay. She even tries to portray herself as just a kindly old lady, ala Mom from Futurama. Crock is a more mundane kind of evil than Mom, though.

But Norm MacDonald's never been a favorite of mine, so having him as the lead isn't great. He can't really convey any emotion without it feeling like he's smirking the whole time. Even when he's supposed to be in a panic, it doesn't quite carry. But Dave Chappelle and Danny DeVito are always fun. Most of the laughs in the movie come from the two of them, since they both just lean into the stupidity and go with it. Sarah Silverman's in there as MacDonald's girlfriend, I guess. She seems to just pop up three or four times when the plot requires someone else to do something.