Chaotic Facts About Val Kilmer, The Modern Casanova

March 20, 2023 | Edward Sakowsky

Chaotic Facts About Val Kilmer, The Modern Casanova

Val Kilmer is a lot more complicated than the action star we know from the screen—his life behind the scenes was somehow even more fast-paced. Born into a relatively normal family, his youth was anything but. Because of his bizarre behavior and his shocking affairs, this now-ailing star is a modern-day Casanova. An action film could easily be made from his memoirs. Continue reading to discover his rollercoaster ride of a life.

1. He Was Born On New Year’s Eve

The actor known for his role as Iceman in Top Gun was born on December 31, 1959, with mixed German, Irish, Swedish, and Cherokee ancestry. The second son out of three, you might think being born on New Year's Eve had Kilmer fated for exciting things. But first, a series of tragedies awaited him.


2. His Parents Divorced Early

It’s a heartbreaking experience for any child to see their parents divorce. It’s especially harrowing when it happens while they're still in elementary school. Val Kilmer was only eight years old when his mother and father decided to call it quits. As if that wasn’t a bad enough way to start a childhood, there were far worse things in store.

Val Kilmer factsTop Gun (1986), Jerry Bruckheimer Films

3. Tragedy Struck His Family

Other than his parents divorcing, the Kilmer household seemed to be carrying along fine. In 1977, however, something changed Kilmer's life forever. Wesley, his younger, epileptic brother, was relaxing in a jacuzzi when he became unresponsive. He never regained consciousness. He was only 15.

Despite such trials in his youth, however, Kilmer wasn’t only a magnet for tragedy. Many extraordinary things would soon happen to him.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

4. He Went To Highschool With Famous People

Maybe there was something in the water at Kilmer's high school; he wasn't the only future star to attend Chatsworth High School. Other would-be famous (or infamous) celebs who attended the school with Kilmer include Kevin Spacey and Emmy-winner Mare Winningham. Spacey and Kilmer weren't exactly friends—while he and Winningham were a lot more than that.

Val Kilmer factsWikimedia Commons

5. They Became Pretty Close

Just like any high school melodrama, soon-to-be actors Kilmer and Winningham started dating while still in secondary school. They were only teenagers when they fell in love—well, at least Kilmer fell in love. More than that even. His love was by no means healthy. He became dangerously obsessed with her, and the relationship made him do crazy things.

Michelle Pfeiffer factsShutterstock

6. He Was Obsessive

Kilmer's obsession with Winningham made him to do some crazy things. He once dreamed she was cheating on him—kissing someone else, to be exact. After he woke up, he borrowed someone’s car in order to drive at least 300 miles to find her. Was the trip eventually worth it? Well, his journey yielded some rather surprising results.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

7. His Dream Was Prophetic

Kilmer must have had a detective’s intuition, because he found Winningham at a swimming club after traveling hundreds of miles. She was there...and she was kissing someone, or at least so he claims. Amazing coincidence, huh? Maybe he wasn’t so crazy after all! Young love isn’t always just a bed of roses. Luckily, he had other things to look forward to.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

8. He Was Accepted Into A Legendary School

What better way to get back at an ex than to better yourself? Val landed a spot in one of the finest acting schools in North America: New York's Juilliard School. Surprisingly, he soon ran into someone from his old high school—though not exactly a face you'd be happy to see. His classmate Kevin Spacey got into the school as well—but Kilmer already despised Spacey at that point.

Val Kilmer factsShutterstock

9. He Was A Prodigy

Horrible friends aside, Val was a pretty smart guy. At 17, he was the youngest student in his entire university class. At the time, he was also the youngest person to ever be accepted into Julliard, a record that stood for decades. With that sort of fame, it’s no wonder he acted out in strange ways.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

10. He Turned Down A Legendary Director

With as much momentum as Kilmer had, it might not seem too surprising that he turned down Francis Ford Coppola. In 1983, the director of The Godfather offered him a part in The Outsiders, but Val turned him down. It turns out he wasn’t as interested in the project as his own work. The bright lights of the New York stage called to him first.

Kevin Spacey FactsGetty Images

11. He Went To Broadway

Kilmer was more interested in high-class theater than some big-shot director like Coppola. In 1983, he starred in an Off-Broadway production of The Slab Boys with a few other aspiring stars. Kilmer tread the boards alongside Jackie Earle Haley, Kevin Bacon, and Seann Penn. Despite those names, the play was not his major break into stardom. If anything, his next project was a step down.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

12. He Was Sidelined On Television

Kilmer wouldn't be getting any special treatment on television, even if he was one of the Slab Boys. Next, Kilmer ended up in an Afterschool Special called "One Too Many" along with his ex Mare Winningham and Michelle Pfeiffer. Despite the all-star cast, they appeared in one episode. Just one. It wasn't all for nothing though—a scandalous rumor started from this production.

Val Kilmer factsFlickr, Ian W. Hill

13. He Had An Affair With His Co-star

Word gets around fast, and soon people started that there was a "thing" between Kilmer and Pfeiffer. Whether the relationship was requited or not is uncertain, but one thing is: he claims that there was an emotional “intimacy between” them on set, particularly of shared grief. However, there’s a possibility that Val was using Michelle to get even closer to someone else...

Val Kilmer factsWikimedia Commons

14. He Had A Crush On Her Sister

Kilmer practically gets a crush on everyone, but the targets of his affection weren't always appropriate. Michelle’s sister, younger by four years, “did not seem to reciprocate [his love], even a little.” It was about time someone turned down this modern day Casanova. But this one rejection wasn't going to slow Val Kilmer down.

Hollywood Feuds FactsShutterstock

15. He Published His Own Poems

Not only was he able to play as a gentleman, or rake if you prefer, he was also a poet in his own right. In 1988, he self-published his collection of poetry, My Edens After Burns, entirely at his own expense. Sadly, it did not set the literary world on fire. Let’s hope he didn’t quit his day job.

While it might seem as if he was sitting in a corner, scrawling deep metaphors, there’s actually something else quite racy about these poems.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

16. He Wrote About His Costar

Val Kilmer didn't just write any poems—he wrote poems about Michelle Pfeiffer. That means Michelle Pfeiffer was his muse. It’s difficult to find anything that screams romance as much as a guy writing poems about a girl. It’s even cliche. Sadly, if anything did happen between them, they hid it rather well, because nothing more seemed to come of it. However, he wasn’t only lucky with the ladies.

Val Kilmer factsShutterstock

17. He Was Forced Into His Most Famous Role

It turns out, Val Kilmer's agent was a little more farsighted than he. Initially, Kilmer had no intention of playing alongside Tom Cruise in Top Gun, one of his most famous roles to date. He even had moralistic qualms about the project, thinking it was a work of propaganda. He was lucky that the director, Tony Scott, was obsessed with him. Scott just had to have Kilmer audition for the role of Iceman.

Val Kilmer factsWikimedia Commons

18. He Purposely Botched The Audition

Kilmer did everything in his power to not land the role. He claims he “read the lines indifferently,” and was amazed when he found out he scored the part. In fact, he even tried to run away after. The director chased him all the way to the elevator and only managed to stop him by heroically thrusting his hand into the closing door. Sometimes life really is stranger than fiction.

Val Kilmer factsTop Gun (1986), Jerry Bruckheimer Films

19. He Was Catapulted Into Stardom

Today, when people think of Val Kilmer, Top Gun comes to mind, though he tried hard to avoid it. It's almost as if he was fated for stardom. Internationally, the film grossed over $340 million, nearly unheard of at the time. Val Kilmer was now a major star, a household name not only in America, but also the world. And while the man was now a legend, the legend was also a man.

In fact, his masculinity might be his biggest concern, as soon became apparent.

Val Kilmer factsTop Gun (1986), Jerry Bruckheimer Films

20. He Declined To Meet A Famous Popstar

A matchmaker friend of Kilmer's wanted him to meet with a legendary popstar—though he admittedly needed some convincing before he agreed to meet Cher. His friend told him that if he did not find her “compelling, [he] could leave.” He ended up enjoying the meetup. He even thought she was hilarious, enough to drive her back home on his “Harley through the streets of Manhattan.” Oh, but the story doesn't end there.

Val Kilmer factsPicryl

21. He Loved A Much Older Woman

They must have hit it off really well, because Kilmer and Cher became inseparable. The legendary pop star was over 10 years his senior, but that didn’t stop them from falling in love. He described her as an artist “who displays the attributes of a child, teenager, and sagacious adult all at once.” Maybe it was the energy that drew him to her. He even displayed a poster of her in one of his films. Good things, however, often do not last.

Val Kilmer factsWikimedia Commons

22. They Remained Good Friends

Large age gaps, even in Hollywood, often cause issues in relationships. Val and Cher were not to last. They broke things off, but even then, he had some glowing words for his former lover. He said that she was “forever [a] friend, [and the] funniest woman I ever met.” How heartwarming—although, the Top Gun star wasn’t one to remain alone for long.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

23. He Became Infatuated By Another Co-star

Kilmer became obsessed with his next co-star even before he met her. Val was scheduled to play in another blockbuster film, Willow, alongside Joanne Whalley, who was at least age-appropriate. He claims she began haunting him before they had even met. But what seems a little strange for most people is absolutely normal in Hollywood. Just wait and see.

Val Kilmer factsShutterstock

24. He Married His Co-star

The stars again aligned for Val Kilmer. The woman he obsessed over would play his wife alongside him in his upcoming film. He must have been a quick worker, because they were ready to tie the knot within the year. In 1988, one year after meeting Whalley, they were husband and wife. Despite such a lightning start to their relationship, he wasn’t exactly the best spouse.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

25. He Was A Neglectful Husband

One’s honeymoon is usually an ecstatic time. Kilmer, however, felt the need to study a play. In fact, he studied it every single day of their honeymoon. As you can imagine, Joanne was far from impressed. Kilmer understood, and even called it justifiable—but it’s a lot easier to admit that long after the fact. Maybe they should have just called it quits right there. Instead, they did the exact opposite...

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

26. They Had Two Children

Even a bad honeymoon didn’t stop these stars. Instead, they had children. In 1991, Joanne gave birth to a healthy daughter named Mercedes. They decided one wasn’t enough, so four years later, she had a son named Jack. Was it the old cliche again? Can children really fix a marriage? Or was the marriage already doomed?

Val Kilmer factsGetty Images

27. His Wife Sacrificed Her Career For Him

It’s difficult to take care of kids, even if that’s the only thing you’re doing. It’s even more difficult to take care of kids if you’re working a full-time job with an erratic schedule. Joanne took a break from her career to bring up their children. It’s possible she was also attempting to salvage their marriage. Kilmer? Not so much. Some things just aren’t meant to be.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

28. Their Marriage Didn’t Last

After nearly a decade of marriage, Kilmer and Whalley went their own ways. In a condemnation of his personality, his wife once told him that he “get[s] crushes on everything.” Ouch, seems like she was fed up with his Casanova-like antics. Their children were less than a few years old when they separated. Guess it didn’t fix their marriage after all. In fact, if anything, it made things worse.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

29. They Had A Ruthless Battle Over Custody

Both of the stars wanted custody over their children, and so both went head to head in court. It’s said that divorce is a conflict with no victors. Luckily, both actors eventually shared custody. The kids were going to spend time with both of their parents. Yet while Val fought for his children, he couldn’t stop himself from goggling over another celebrity.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

30. He Met A Famous Supermodel At An Afterparty

Before divorce proceedings had finished, Val Kilmer was already doing what he did best. That is, frequenting parties in the hope of another fling. In 1995, he met supermodel Cindy Crawford at the premiere of Batman Forever. You can just imagine what goes down at those parties. Even before Kilmer's marriage was completely over, he and Crawford became inseparable—but was she ready for Kilmer's mess?

Val Kilmer factsWikimedia Commons

31. He Was Hopelessly In Love With Her

It seems that the words of his ex-wife were spot on, Val really did get a crush on everyone. Crawford apparently consoled him during his divorce. He even says he “could have [perished] from her love.” That makes her the human equivalent of a black widow. That’s a backhanded compliment if there ever was one. Was this relationship finally going to last?

Val Kilmer factsWikimedia Commons

32. They Dated For A Long Time

Val Kilmer dated Cindy Crawford for a decent amount of time. For his standards, that is. For two whole years, to be exact. Not only was she a supermodel, but she was intelligent, charismatic, and a great cook. However, they never chose to marry, and no one really knows why. It’s possible that Val just needed to recover after his heartbreaking divorce—but regardless, there was more in store for this pair.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

33. They Parted Amicably

Quick flings and amicable partings could be a chapter in the memoir of Val Kilmer. It could even be the whole book. After being together for some time, he and Crawford chose to put an end to things—but as far as breakups go, this was quite mature. They had a heartfelt conversation about their future and decided together what was best for them.

If only all relationships could end that way. The star was not nearly as gentle in his professional life.

Val Kilmer factsFlickr, rocor

34. He Worked Dangerously

Val Kilmer was known for doing his own stunts on some sets. When he played Jim Morrison in The Doors, he dove into the crowd during one scene. Someone was supposed to catch him...they didn’t, and he broke his arm. That’s enough to give anyone trust issues. But while the dangerous stunts were one thing, there was something else about him that people despised.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

35. He Was Notoriously Difficult To Work With

Ask just about anyone who's worked with him: Val Kilmer can be a nightmare to work with. Joel Schumacher, the director of Batman Forever, called him “childish and impossible.” It’s almost like the child actor had never grown up. There were tons of horror stories circulated regarding this production—it's little wonder he didn't come back for Batman & Robin.

Val Kilmer factsWikimedia Commons

36. He Was Explosive On Set

Val Kilmer was confrontational and aggressive with pretty much everyone in the cast and crew for Batman Forever. Leave it to Val to turn a film set into a colosseum. Whether it’s an exchange of harsh words or punches, the action film star really lived up to his name. But it wasn't all blowups and jabs—Kilmer could be unbelievably childish as well.

Val Kilmer factsBatman Forever (1995), Warner Bros

37. He Took A Vow Of Silence

Joel Schumacher, fed up with Kilmer's antics, finally had it out with him one day on set. Surprisingly mature, Schumacher told Kilmer he was being rude and to behave like a normal person. Well, that was apparently too much for Val. In his prettiest move yet, the star took a vow of silence. He chose not to speak to the director for at least two weeks. I guess he really was “childish and impossible” after all. And people weren’t always as nice as Schumacher, as we’ll see.

Val Kilmer factsBatman Forever (1995), Warner Bros

38. He Caused A Director To Get Fired

Kilmer's antics were horrendous, to say the least, and he wasn't getting any better. He arrived two days late to the set of The Island of Dr. Moreau. That means everyone had to wait for him in order to start production. Not only that, but he never cooperated, almost as if he was intentionally wasting everyone’s time. His co-star Rob Morrow even ended up crying, saying he wanted to resign from the project.

And in the end, someone else faced the consequences: The studio fired the director, but Kilmer remained the star. Great job, Val—yet his next feud was somehow even more hostile.

Val Kilmer factsWikimedia Commons

39. He Had A Publicized Feud With His Replacement

When the next director, John Frankenheimer, arrived, it became clear things would be a little different. He and Kilmer constantly fought with each other, never seeing eye to eye. Val, who was often opinionative, once gave John a suggestion. The latter responded by saying “I don’t give a [bleep], get off my set.” Val had finally met his match, it seems. Surprisingly, there was an even bigger conflict on that set than this one.

Val Kilmer factsWikimedia Commons

40. A Legendary Actor Hated Him

Marlon Brando’s feud with Val Kilmer is the stuff of legends. Brando once told Val that his “problem” is that he “confuse[s] [his] talent with the size of [his] paycheck.” Ouch. It escalated to the point of a full-blown stand-off. Both actors refused to come out of their respective trailers. They didn’t want to see each other on set. Reminder: These were the two stars of the film.

With this sort of behavior on set, it’s a wonder how any films get made at all...

Val Kilmer factsFlickr, oneredsf1

41. He Found A Soulmate In His Costar

With all of that fighting going down between Kilmer and his co-stars, it’s no surprise that he sometimes needed to settle down. He met Daryl Hannah while filming Hard Crash. The film was a critical and financial flop, but they must have hit it off. They started dating, and, as he was wont to do, Kilmer became infatuated with her. This relationship would be, you guessed it: A total trainwreck.

Val Kilmer factsWikimedia Commons

42. He Was Infatuated By Her Snowboard

At least Kilmer and Hannah shared a hilarious moment together before everything went south. When Hannah brought her new beau to her barn, he saw a sculpture that immediately won him over. He referred to it as a “daring piece of avant-garde sculpture,” and that he had to know who created it. Imagine his face when he discovered it was...a snowboard. He really did get a crush on everything.

Peaceful moments like these, however, were few and far between for this couple.

Val Kilmer factsBatman Forever (1995), Warner Bros

43. They Had A Chaotic Relationship

Kilmer and Hannah had a tumultuous love. He memorably describes their romance as “a beautiful storm followed by a priceless rainbow,” and that they “loved deeply and fought deeply.” How poetic. Unfortunately, that rainbow never lasted for long...

Val Kilmer factsWikimedia Commons

44. He Was Deeply Wounded

As he did with all his crushes, Kilmer eventually drove Darryl Hannah away. He thinks maybe he was too jealous or had too much of an ego, but he isn’t certain (Our guess? Both and more). To this day, the Top Gun star doesn’t know exactly why Hannah left him. Two decades later, he still remembers the pain this split caused him. He gave up on dating. He also cast aside the goal of finding “the perfect wife,” and looked toward other things.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

45. He Became More Spiritual

Instead of finding fulfillment through others, Val Kilmer looked to himself. After his devastating breakup, he refocused his energy into “equally wild and mystical avenues.” One of those avenues is his faith, Christian Science. He claims that his faith strengthens him, and without it, he “would be lost.” Unfortunately, tragedy awaited him nonetheless.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

46. He Was Dangerously Sick

In 2015, Kilmer ended up in the hospital with a terrifying ailment. His throat had a malignant tumor. It was cancer, and he needed surgery. Things looked grim at first for the star. The process took a bright turn, though, after his hospitalization. After battling the disease for years, he fully recovered. However, he responded very strangely to rumors about his cancer.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

47. He Strangely Denied It

The Top Gun star denied rumors about ever having the disease. Why do that? Did he not want the publicity? That’s a possibility. But he even went as far as to deny these rumors on social media. He claimed that he never had cancer, nor even an operation for it. It’s impossible to tell why he did that. Of course, he couldn’t keep this information a secret for long—especially because of its consequences.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

48. He Has An Unfortunate Problem

Val Kilmer's story unfortunately has a sad conclusion. Well, there’s good news, and there’s bad news. He’s still alive. That’s the good news, but his throat cancer has left him in an unpleasant state. Tracheostomies have left him permanently short of breath, and requiring him to always feed from a tube. In order to communicate, he also needs an electric voice box, which is plugged into him. It’s a rather disheartening end for an actor who once nearly soared as high as the stars.

Val Kilmer factsVAL, Val Kilmer Documentary (2021), IAC

49. His Family Was Scammed By His Schoolmate

Val Kilmer is one of the most complicated men in Hollywood history, but let's not forget who the real bad guy is in this story: Kevin Spacy. Years before the depths of his depravity came out, Kevin Spacey tricked Kilmer's father Eugene into giving him money. Spacey allegedly played it off as being desperately in need of money for tuition, claiming he would drop out if he couldn't find the money to pay Eugene back.

Since he and Kevin went to high school together, Eugene wrote him a check for $18,000. Of course, the Kilmers never saw that money again.

Val Kilmer factsWikimedia Commons

Sources: 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15

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