If you are thinking of renting or purchasing this film, be advised that the promotional poster and DVD cover is deceptive. Denise Richards does not appear in those black leather pants or in any outfit that is particularly hot. On the other hand 2001 was the absolute peak of her attractiveness. She was into a serious fitness thing which brought her weight down, doing very good things for her face. And she was a good fit for the role, which capitalizes nicely on her Jane Russell/Megan Fox type negative charisma; and on Richard's own general vacuity.
The other casting choices were not as good. Writer/director Brian Burns is trying for the "Annie Hall" - "When Harry Met Sally" crowd and wants David Krumholz (Bernard of "Santa Clause" fame) to sell himself as a Woody Allen like nebbish in the middle of a love triangle with two extremely beautiful women. Unfortunately this oily actor looks like the sort of guy who would proposition your 14-year old sister. Not anyone you want to identify with nor anyone who brings out your sympathy vote.
Milla Jovovich is a talented actress who has appeared in way too many bad films; most much worse than this one. She is hopelessly miscast physically in "You Stupid Man" where her character's plainness is supposed to contrast with the dazzle of Richard's character. Despite this she manages to sell her character; although you never remotely buy into her love for "Meet Me in St. Louis"; her rendition of "The Trolley Song" is genuinely painful. If you are a fan of that classic musical I suggest giving "You Stupid Man" a wide berth as Burns makes it the awkward leitmotif of the Krumholz/Jovovich relationship (insert "yuck" here).
Burns has written a decent script, a little light on comedy or at least comedy that works, but its social commentary gets high marks. Too much of a NYC consciousness probably hurts this thing with a national audience.
Then again, what do I know? I'm only a child.