Unfortunately, Val Kilmer left his legacy behind at the age of 65, on April 1, 2025. From now onwards his legacy will be cherished through his onscreen performances alongside the likes of Tom Cruise and Al Pacino. But on this heartbreaking occasion, we came across something even more tormenting—Kilmer’s last regret surrounding Robert Downey Jr.
After collaborating with Robert Downey Jr. in Kiss Kiss Bang Bang, while Val Kilmer admitted having fond memories from the set, he also admitted having a heartbreaking regret about Downey Jr. that left him feeling blindsided. Seven years ago, in a Reddit AMA, Kilmer shared how a surprising incident with the MCU star and Michelle Monaghan broke his heart.

Val Kilmer’s heartbreaking regret about Robert Downey Jr.
Val Kilmer might have appeared in a bunch of movies that remained cult classics through generations, but nothing stood close to his 2005 movie Kiss Kiss Bang Bang, alongside Robert Downey Jr. From electric chemistry to unmatched comedic timing, Kilmer and Downey Jr. turned the movie into a fan-favorite crime comedy.
So much so, that even Val Kilmer openly appreciated his collaboration with Robert Downey Jr., director Shane Black, and even his co-star Michelle Monaghan, during a Reddit AMA. But while addressing the fun they had behind the scenes, Kilmer reflected on an incident he wished had gone differently—the one that left him feeling blindsided.
I love those guys so much and we had so much fun. You can tell if you watch the behind-the-scenes footage. I ruin so many takes cause Downey has me howling that he actually gets upset and demands I “Keep going keep going…”
And Shane is just the best. So unusual. So clever. And then RDJ went and worked with Michelle Monaghan and didn’t even tell me. I woulda gone by just to watch them together again.
During the Reddit AMA seven years ago, Val Kilmer opened up about the joyful experience he had on set with Robert Downey Jr. and Michelle Monaghan. But then he opened up about hoping for further collaboration with his co-stars until he found out how Downey Jr. and Monaghan joined forces in the 2010 movie Due Date.

The actor shared that Robert Downey Jr. and Michelle Monaghan had signed the movie, appeared in it, and promoted it, all without letting Val Kilmer know. He then mentioned how much that stung, especially since he would have joined the duo had he known about the project. So now, based on the weight of disappointment that his words carried, it seems Kilmer was heartbroken.
Val Kilmer passed away from pneumonia at age 65
For someone like Val Kilmer, who always valued deep connections with his co-stars, being left out must have hurt. And now, after his passing, this small regret feels even more heartbreaking.
On April 1, 2025, the renowned actor known for his unforgettable roles in Top Gun and Batman Forever passed away at the age of 65 due to pneumonia. His daughter, Mercedes Kilmer, informed The New York Times about the actor’s demise in Los Angeles, after battling with throat cancer.
After suffering from throat cancer for years, Val Kilmer had gone public about his ailment, which left him with a permanent loss of voice. However, although the disease took his voice, it could never steal his spirit. Through it all, the late legend remained dedicated to his craft, continuing to act and write.

The late legend lived on a ranch in New Mexico for several years, where he mostly spent his days painting and helping oversee theater programs for high schoolers. He married Joanne Whalley in 1988 but divorced her in 1996. Kilmer is now survived by his daughter, Mercedes, and son, Jack.
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