Kiss Kiss Bang Bang
Saw Kiss Kiss Bang Bang starring Robert Downey Jr., Val Kilmer, and this total hottie named Michelle Monaghan, and dug the hell out of it. But then I like self-referential movies that break the fourth wall. When it's done well, as it is here, it actually sinks me deeper into the movie because it feels like I'm in on the joke.
The premise is Downey is a small-time thief who evades arrest by happing into a film casting session. The scene he reads so closely resembles what's really happening to him that they cast him on the spot as a detective. The movie folks hire a real detective, Val Kilmer, to train him to act more like a private eye. Hilarity ensues.
Besides the fact that the movie is funny and sexy, I love the way two of the characters are handled. First, the female lead is refreshingly complex and has some great twists to her character, and some great laugh lines. Second, Val Kilmer's character is gay, and FOR ONCE, it's not the "obligatory gay character" that has infiltrated too many recent films (if you don't know to what I refer, then I prolly couldn't explain it). The fact that he's gay is just that, a fact, and all the plot points that touch upon that fact are crucial to the plot. In other words, it's realistic. And damned funny.
When looking up some info about the film (re what in the hell else did Shane Black do?; ans: Lethal Weapon), I discovered that the original casting choices were Hugh Grant and Benicio Del Toro. Downey and Kilmer are both so perfect for their respective roles, it simply would not be the movie it is without them.
It's odd this movie wasn't bigger. If you haven't already, you should check this little jem out.