The Cooler (2003)

  I've never been a huge fan of William H. Macy.  He's always been just another character actor to me, not really a leading man.  Maybe because he looks so sad all the time.  Look at him.  Even in neon, he's like Droopy Dog.

Which is precisely what his character needs to be in this movie.  Bernie Lootz is a Cooler, a man employed by a casino because he causes everyone at a table to lose.  Casinos like it when people lose.  Especially this casino, because it's owned by Alec Baldwin.  See, Alec is facing some difficulties because his Golden Shangri-La is one of the last few old-school casinos left in Vegas and he is under pressure to show that it can still be a moneymaker.  Ron (Office Space) Livingston is an up-and-coming player trying to take Baldwin's place.  So when Alec's best Cooler decides to call it quits, he hires Maria Bello to honeypot the poor schmuck into staying.

Unfortunately for Alec, she turns out to be Bernie's lady Luck and now he has to do everything he can to break them up.

This is a cute, if dark, film with a great cast.  Alec Baldwin was nominated for Best Supporting Actor (lost to Tim Robbins for Mystic River) and Macy and Bello are both note-perfect.  I have always appreciated Maria's willingness to "ugly up" for a role.  That and she seems to have no problems getting naked either.  It moves a lot slower than I would have liked but still a good movie.