He was an A-lister from his appearance in the original Top Gun in 1986 and remained a big star into the '90s but it seems he wasn't uptight about playing supporting roles. His supporting roles in Tombstone and Heat are certainly memorable. The latter film, which has lately garnered a lot of attention, is considered one of the greatest crime dramas of all time and his role was integral to it.
I saw him in person at San Diego Comic Con in 2010 when he was there to promote Twixt with its director, Francis Ford Coppola. A remarkable experiment, it was initially Coppola's plan to edit the film live based on audience reactions. Coppola demonstrated by showing us a trailer edited live. The audience that day responded most warmly to shots of Kilmer's character being foolish, drunk, and funny.
He was excellent as Jim Morrison in The Doors biopic, though I'm not the greatest fan of its director. I also enjoyed seeing him pop up in films like Werner Herzog's Bad Lieutenant: Port of Call New Orleans and Kevin Smith's Jay and Silent Bob: Reboot.
For me, though, his greatest role will always be Madmartigan, the "greatest swordsman who ever lived" in the fantasy film Willow. I always loved the European Middle Ages and medieaval fantasy films in particular. When Willow came out in 1988, I was nine years old and it was fantastic.
Sure, the comedy's a little broad and Willow is hardly the finest George Lucas film but Kilmer as Madmartigan exemplified the kind of cinematic hero Lucas and Spielberg were creating; a guy a who makes mistakes and who is sometimes misled by his passions. No fascist hero was Indiana Jones or Madmartigan, even when they were also larger than life. These were human heroes for humans. I, for one, think humanity benefited and I thank Val Kilmer for his part in it.
X Sonnet 1930
Electric blue were words of ancient force.
But boats of twisted reeds conduct a hope.
The winding brook conforms to serpent's course.
The rocks would roll along the broken slope.
As gods of wine beheld their own, they wept.
The mighty sword would rust as trolls would rule.
Within expectant hearts, the dream was kept.
The gun of Holiday's a quiet tool.
The stately raven churned the film of yore.
In days of heat, the lucky thief was warned.
His song would lead us through a spirit door.
No shrink could shrink the bat when scorned.
It seems there's naught for little men to do.
And still he says he'll win this war for you.