Val Kilmer did not receive an Oscar nomination, despite winning a Satellite award (yes that award is considered a bit of a joke but hey they awarded Javier Bardem for Skyfall so they can reward a good performance), for portraying "Gay" Perry van Shrike in Kiss Kiss Bang Bang.
I might as well not beat about the bush and say that Kilmer is a joy to watch in this film as he, like Robert Downey Jr, knows just how to play the material. As Downey does in his lead performance he finds just the right tone for his performance being slightly comic throughout yet displaying such an ease with the more dramatic moments as well. Kilmer though is slightly different here as he is the supporting player whereas Downey is the lead. Kilmer properly makes Perry less sympathetic than Harry, although still very likable, but he properly has a more cynical edge that causes him to differ from Downey' performance.
Kilmer is great in the role as he takes a bit of a rougher approach to some of the material that work particularly well for the film, as well as does a lot to emphasize the experience that Perry has in the sort of matters that take place in the film oppose to Harry who is a bit more of a freshman. Kilmer is properly convincing in the role as Perry and Harry deal with the mystery. Kilmer has the proper conviction and strength in the role to properly suit the mentorish properties of Perry. Kilmer exudes just the right degree of confidence in the role that works well in the film, almost being a comforting factor at times because he shows Perry to be just about always on the ball.
Val Kilmer most importantly has terrific chemistry with Robert Downey Jr. They are just a great duo throughout the film, and they play off each other wonderfully making all of their scenes together delightful. Kilmer is excellent playing Perry as the smarter older, although less passionate of the two. He is particularly great in any scene where Perry straightens out Harry a little bit for the dumb decision he makes time to time. Kilmer is always hilarious in these moments having just the right bluntness in the moments. The two are just perfect together in their antagonistic scenes always bringing out the humor in their conflict brilliantly.
This is a very entertaining performance bringing the best out of the script of the film, and even out of Robert Downey Jr. They both just play the scenes so well that they do not overshadow each other than just amplify each other. Val Kilmer turns his mentor/partner character into just an extremely likable character throughout the film. Kilmer's performance here just works to the point that I have to admit I was very relieved when Perry was alive for no sensible reason at the end of the film other than Perry is just awesome. Kilmer is the one who makes Perry as awesome as he is. Kilmer gives another fantastic characterization here, and shows along with Tombstone that it is shame his talent is not exploited more often.