Val Kilmer’s launch into stardom in the 1980s, his string of hits in the '90s, and his subsequent disappearance from Hollywood is a fascinating story. Kilmer was among the most in-demand leading men in the industry; he was Batman, but he could also play the loveable goofball or the romantic lead.

Yet after lending his vocal talents to 1998’s The Prince of Egypt, Kilmer’s career seemingly phased out as he was replaced by a new generation of leading actors. Although he worked frequently and sometimes chose interesting supporting roles, Kilmer’s stardom became a thing of the past.

So what exactly happened to the man who embodied Doc Holliday, Bruce Wayne, and Jim Morrison? Kilmer’s memoir I’m Your Huckleberry, released last year, helped to explain the direction his career turned. Kilmer discussed the severe toll that media objectification and his recovery from throat cancer had on his health and well-being, giving a window into his personal struggles which had largely been kept private. Amazon Studios recently acquired Val, a documentary project shot over the last 40 years, which is set to provide an unflinching look at Kilmer’s highs and lows. He’s also set to return to one of his most iconic roles this fall in Top Gun: Maverick, in which he’ll reprise his role as Iceman after 35 years. These projects make it a better time than ever to reflect on his most defining roles to date.

Narrowing down Kilmer’s most essential work is a challenging task; he has a diverse filmography that shows different strengths. It’s tough not to include his breakout role in Real Genius, his brilliant supporting role in True Romance, or idiosyncratic character roles in more recent projects like Bad Lieutenant: Port of Call New Orleans or Palo Alto. There’s no more “gif-able” character than Top Gun’s Iceman, and there’s certainly a case to be made that he was a pretty solid Batman and arguably deserved more credit for his interpretation.

These performances, though, should hopefully provide a good prep that explores the different facets of Kilmer’s work. Here are his seven most essential performances.

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7. Simon Templar, The Saint

Simon Templar driving a car and looking to his back in The Saint
Image via Paramount Pictures

The Saint is a very, very silly movie. It’s unclear why the character of Simon Templar needed a tragic origin story, or what exactly his goals are beyond a general need to rebel against his religious upbringing. Roger Moore played the character as a Bond-to-be in the original series that inspired the film, and this 1997 action-heist-thriller adaptation never finds quite the right mix between hokey and clever.

Yet, Kilmer makes it almost compulsively watchable, wearing all sorts of ridiculous disguises, prosthetics, and makeup with a winking grin. The '90s gadgetry has aged the film into a digestible campy romp, and the melodramatic romance with Elizabeth Shue is played so straight that it feels like it could be revealed as a gag at any moment. The implausibility of the heists and strange biblical references are certainly never dull. Kilmer may have earned a Razzie nomination for his performance, but it’s such a weird role that it’s kind of hard not to at least admire.

6. Madmartigan, Willow

Val Kilmer as Madmartigan in Willow 1988
Image via MGM

There are those that grew up with Willow, and those who watched it later in life. I fall into the prior category, and it’s admittedly not one of the '80s adventure films that have become timeless. Yet even if you ignore the nostalgia, Willow is a lot of fun. It’s less stuffy and more endearing than a lot of Lord of the Rings wannabes from the era, and certainly more enjoyable than recent Game of Thrones knock-offs have been. There’s a mythology there, but it’s essentially a fairy tale with goofy side characters, terrific practical effects, and a heartwarming performance at the center by Warwick Davis.

It’s more than obvious that writer/producer George Lucas intended for the character Madmartigan to be the stock “Han Solo” character of his fantasy epic, and Kilmer nails the role of a rogue mercenary with a heart of gold. The same sort of wry humor and skepticism towards magic that Harrison Ford brought to the original Star Wars films is what Kilmer does here, and it’s perhaps even more important considering how wacky Willow’s fantastical elements get. Kilmer can also pull off sincerity in an endearing way, and Madmartigan’s budding romance with Sorsha (Joanne Whalley, who briefly became Kilmer’s real-life partner) is surprisingly touching.

5. Chris Shiherlis, Heat

Val Kilmer in Heat
Image via Warner Bros.

Heat is one of the hardest Kilmer performances to rank; it’s easily the best movie he's ever been in, yet it’s so clearly a showcase for Robert De Niro and Al Pacino. Kilmer’s performance is absolutely necessary in filling out the ensemble, particularly in decoding the moral values of De Niro’s Neil McCauley, but it's obviously secondary to the thrill of seeing the two leads in their iconic first scene together.

Kilmer is so good in it though; he’s able to stand toe-to-toe with the generation’s greatest actors and bring his singular physical presence to the influential setpieces. The romance with Ashley Judd is the type of subplot that should feel like a hindrance, but Kilmer makes it surprisingly emotional and doesn’t break the meticulous pacing. Released the same year as Batman Forever, it’s admirable that Kilmer also understood when he didn’t need to be the star.

4. Doc Holliday, Tombstone

Val Kilmer in Tombstone
Image via Walt Disney Studios

If Heat showed how Kilmer could integrate himself as a supporting ensemble player, Tombstone showed his ability to outclass and outcharm his co-stars. The stacked lineup of performers in Tombstone is just as impressive now as it was in 1993, but Kilmer somehow manages to be the standout, and his Doc Holliday is a perfect blend of the machismo, humor, and romanticism that he excels at.

Tombstone’s cheeky sincerity is partially why it was such a novelty within the western genre during release, especially compared to the revisionist approach of Clint Eastwood’s Unforgiven the year prior. Kilmer is just effortlessly cool and embodies Holliday’s arrogant presence, yet he can also make the final moments with Kurt Russell rather touching without feeling out of left field. In a film where every character feels written to be the scene-stealer, Kilmer walks away with the honor.

3. Perry Van Shrike, Kiss Kiss Bang Bang

Val Kilmer in Kiss Kiss Bang Bang
Image via Warner Bros.

Kiss Kiss Bang Bang is often discussed as the film that relaunched Robert Downey Jr.’s career before 2008 gave him both Iron Man and Tropic Thunder, but Kilmer’s comeback performance is equally as impressive. No one saw Shane Black’s subversive reimagining of the buddy cop formula coming, and while Downey’s razor-sharp smartass is essential in framing the self-aware story, Kilmer’s comic aloofness is the perfect pairing. Kilmer impressively keeps Perry’s motivations relatively ambiguous when the backstory of Downey’s Harry Lockhart is explored more deeply.

This is also a much different type of comedic persona than Kilmer had ever attempted before. If his early comedic appeal came from charismatic overconfidence and emotional nakedness, the role as “Gay” Perry is completely restrained and emotionally closed off. The jokes land not because of the physical comedy, but because of Kilmer’s blunt line delivery of Black’s comic wordplay. It signified a different, but just as exciting, new chapter in his career.

2. Jim Morrison, The Doors

the-doors-val-kilmer
Image via TriStar Pictures

The Doors is a lot, and at 141 minutes it frequently gives into Stone’s indulgences. Kilmer is perfectly cast and looks the part, but his performance goes deeper than just a reenactment. He perfectly embodies Morrison’s rebellious streak and aptitude for pushing boundaries.

30 years later, The Doors has aged quite well in comparison to other recent musician biopics; it doesn’t deify Morrison and erase his flaws, nor does it try to pin down his entire personality based on a few key experiences. The hallucinogenic early sequences of Morrison’s early inspirations are experimental in a way that breaks from Stone’s standard formalism, and the tonal shifts fit the temperamental personality at the center. Morrison’s defiant performance of “Light My Fire” with its overt drug references on The Ed Sullivan Show is played completely for laughs, but his profane rendition of “The End” at Whiskey a Go-Go does explain just how aggravating he could be. It’s a really well-rounded performance that holds the overlong film together.

1. Nick Rivers, Top Secret!

Val Kilmer in Top Secret!
Image via Paramount Pictures

Top Secret! is a straight-up masterpiece of the spoof genre. Spoof films aren’t necessarily suited for longevity, as jokes are often references to a specific moment in pop culture, but Top Secret! is so loaded with gags that it doesn’t matter if they don’t all land because the momentum is never lost. The references are also just broad enough; even if you’ve never seen a John Frankenheimer spy thriller or an Elvis Presley vanity project, you can pick up on the trends Top Secret! is satirizing. It’s just a fun action-comedy, period, and Kilmer shows remarkable ease with the genre-hopping storyline in his first feature role.

Although it would’ve been easy to simply adopt the same sort of hapless authority character that Leslie Nielson made famous in the Naked Gun franchise, Nick Rivers isn’t a buffoon. If spoof films often aim for the lowest common denominator jokes, then Top Secret! actually aims for some more sophistication with clever sight gags that go beyond cheap parodies. It’s nice to see the lead in a parody film become a real character worth investing in, not just the butt of the joke. While eccentric, his solutions for facing off against the Nazi villains are creative, and it’s clear that he’s choosing to aid the anti-fascist resistance movement of his own accord rather than being roped into it by implausible plot mechanics.

Kilmer’s musical performances are electric, and he’s able to find the right balance between wacky and charming. Co-director David Zucker would later admit that the central threat of German reunification was written broadly enough that the film could incorporate as many setpieces and gags as possible, but Nick’s motivations are always clear. He’s a slightly peculiar guy placed in extreme circumstances, but he steps up to the task with his good-natured spirit. There's nothing that defines Kilmer better than that.

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