In order to get a sizable inheritance, Denis Leary is understated but hilarious as Doug, who must suffer the indignities associated with apologizing all of the women he has betrayed. Elizabeth Hurley, with her impeccably straight laced English accent is perfect as Anna, a rigid, nearly always thoroughly offended lawyer charged with chaperoning him on this perilous journey in what is sure to be the road trip from hell.
The first woman is a crazy cat lady - a wise choice to try to justify why he left her. Never mind that she may have become that way because he dumped her. The next woman is a sex maniac, so one wonders why he would dump that kind of chic. It would have made more sense to keep this one around kicks. Who knows, maybe she was too much for the old boy.
Christine is a militant African American mayor who publicly flogs Doug while he stands in her campaign headquarters. While she clearly used him as an experiment designed to see what would happen if she dated a white man, she is clearly still bitter about the situation. With good measure, she refuses to accept his apology. Anna insists he go back to renegotiate by admitting to disgusting things about himself as she feeds him the words to grovel for forgiveness. She relents. On to his next victim.
Angel is a model who embarrasses him because she doesn't remember their rendezvous. Then she drags him off to a private room while the director says tells the crew to take 5. Only Doug is unable to perform, despite trying to fake it. Again, Anna must listen to them trying to have sex as she waits by the car, but doesn't laugh enough to make the scene funnier. Instead, she modestly cups her hand over her face as if she is discovering something she shouldn't know about.
Emma's picture looks decidedly normal and sweet. She has a daughter and you can pretty well guess what this means. The girl says her mother died and that she does not have a dad. He could be her father, but the kid's granny sends him away. Anna shows some compassion and says she won't count that one.
He finds Erica at a strip joint but she is now a transsexual living as Eric. Then she busts a move using all her stripper guile. She became a man because she was sick of being a doormat. Then she whips out her junk. She says he was the first person she had oral sex with and that he'd told her not to worry that she would get the hang of it. When she finds out he stands to get an inheritance she demands that he perform oral sex on her new manhood. Anna comes to the rescue, just as Eric is beating the crap out of him. So this is the second time that she shows him compassion. We are well on our way to their mating ritual.
Will Sasso is hilarious as white trash trailer park Willy, the sister of the equally hilarious Alex Borstein (both Mad TV alum) who plays Doris. Of course, at least one of the babes he boned must have gotten fat -- so she has blown up like a puffer fish on steroids. Doris relates her tale of woe, telling him how he'd promised to marry her. He admits to being a cad during their high school years. No doubt, he probably deflowered her, too. Maybe there was a reference I missed. She asks for a kiss and then promptly jumps him in anger. I was expecting her to try to put the moves on him, because hot guys always seem to think that all fat chicks want them, despite what a douche they may be. So I was glad to see that instead, she throws him out and refuses to forgive him.
He can't get the little girl he thinks he fathered out of his head and returns to talk to granny. He finds out Emma fell for him, but when she realized she was pregnant, she knew Doug was an ass and didn't want him raising her kid.
Anna finds him weeping in his hotel room, consoles him and says he'll get his million dollars. She says she is not actually married. You know the rest.
Then POW! Anna is actually one of his victims! So she concocted the whole scheme up ... there is no inheritance! She's getting revenge for how he treated her when she was a mousy, bespectacled college student. As if anyone as beautiful as a supermodel like Hurley could ever be ugly.
Of course, he reunites with the daughter he never had. They run into each other and it is revealed that Anna perhaps regrets what he did to Doug to pay him back for breaking her heart. He turns to glance at her and we are supposed to know that eventually, they get together.
I realize it's only a movie, so there was probably not enough time to cover every woman he's ever screwed over - but if this is really all he had, this guy's got no game at all.
Of course, all the while that you know that the script will call for him to get together with his little hot lawyer, Hurley never appears to have much chemistry in this regard with Leary. That's probably a When Harry Met Sally tactic, but I'd still love to be able to ask him what it was like to work with her. In fact, maybe I'll pop him a Twitter and see what he says.
Stay for the out takes. They are worth it!