Wish You Were Dead (2002)
A dark comedy about assassination, insurance fraud, and love found in dire circumstances.
Cary Elwes (think Men in Tights or The Princess Bride, among others) plays Mac, a virgin insurance agent beset upon for his niceness by cruel and malicious Sally Rider (Mary Steenburgen) when she sets out to have him killed for his insurance money, but the hired assassin, Jupiter (Elaine Hendrix), falls for Mac and they scheme against Sally when they find out her evil scheme.
A new scheme that requires Mac to die.
The whole family watched this one, but everyone came away with a different opinion. I liked the film. Along the lines of Drowning Mona or Red Rock West, a lot of twisty interaction occurs. The camera cuts are raw, some of the dialog falls flat or makes leaps, and so much of the comedy is done in the background or tongue-in-cheek.
Jupiter is a man-hating assassin who takes jobs killing adulterous husbands or mean sleazebags. We start the film with her assassinating a cheating meteorologist. She has interludes periodically as she's cleaning up in the Texas town in which the film occurs, until she becomes integral, of course.
Mac is a former desk-jokey insurance investigator being taken under the wing of his mentor and blunt pig of a man, Bruce (Christopher Lloyd). They start out to investigate a claim for auto theft. Mac finds the alleged stolen vehicle, and takes it en-route to his next investigation on a theft claim.
Sally sees Mac pull up in the BMW convertible and assumes he's got money. While poking around the house, he's a bit overwhelmed by Sally's overt advances. She distracts him from looking in the closet (in which they'd stowed the items that were allegedly burgled from their home) by inviting him on a date. The date largely consists of Mac delivering the check for the claim, and Sally "rewarding" him on the kitchen table. He leaves in a fluster after admitting the BMW was not his, leaving his briefcase behind.
In the briefcase, Sally finds his $1 million insurance policy and devises a scheme to get Mac to name her beneficiary, and then kill him for the money; claim she's pregnant.
Sally eventually hires Jupiter to kill Mac. During the time spent together, Mac doesn't strike her as the horrible person that she'd agreed to assassinate. In fact, he becomes smitten with her, and she with him.
Together with Bruce, they scheme to get the million dollars and get other assassins off Mac's back by, getting married, naming his new wife as beneficiary, and then, well, killing him.
Hilarity ensues, I tell you. I recommend it for anyone who likes the dark twisty comedy.