Val Kilmer Felt 'so Bad' About the Way His 1st Meeting With Bob Dylan Went

Val Kilmer was thrilled when Bob Dylan agreed to meet him. Unfortunately, their meeting was more than a little awkward.

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Bob Dylan and Val Kilmer became friends. Their first meeting didn't set a good tone for their relationship, though.

by Emma McKee

Published on April 3, 2025

When Val Kilmer heard Bob Dylan was a fan of one of his films, he decided to try to set up a meeting between them. To his surprise and delight, Dylan agreed. Kilmer said he anticipated the meeting with an almost childlike sense of excitement. Unfortunately, it didn’t go quite as he hoped. Here’s why Kilmer ended up feeling bad about his interaction with Dylan.

Kilmer said he’d grown up idolizing Dylan. When he learned the artist liked the film Tombstone, he figured he could use this to his advantage.

“So Bob Dylan loves Tombstone, it turns out. I found out he was in New York, so I called my friend and said, ‘You know, I’d love to meet him. Is there any chance?’ and he says, ‘I don’t know, I’ll find out,’” Kilmer recalled (via Far Out Magazine). “And the next call I got — I thought it was going to be my friend, but it wasn’t. It was Bob.”

Kilmer said he was so excited that he could hardly believe the situation was real.

“I was real excited, like a crazy fan, like a child; it was so great,” he said. “Basically, it was like nothing. It was like we were old friends, like, ‘You want to come over?’ and he was like, ‘Yeah.’ So he hangs up the phone. I was newly married, and we had a baby, and I went in and said, ‘I think Bob Dylan’s coming over … I’m not sure. It could be a hoax.’”

As it turned out, Dylan’s love of the movie Tombstone became a problem for Kilmer. It was all the singer wanted to talk about, but Kilmer found that he didn’t want to.

“He shows up and sits down, and he wants to talk about Tombstone, but I just can’t, you know, nor can I talk about any of his stuff. Eventually, he says, ‘Ain’t you going to say anything about that movie?’ and I said, ‘Do some “Blowin’ in the Wind” and I’ll…’ That’s what I said to him. Basically, I said no. I get like that sometimes.”

He regretted his obstinacy almost immediately.

“I thought, no one turns this guy down. What was I thinking?”

Kilmer said he wasn’t quite sure why he wasn’t willing to say a few lines for Dylan.

“Anyway, I felt like an idiot afterwards — like, yeah, I could have said a few lines. They’re fun lines too,” he said. “People still ask me to say them, and now I’ll tell any schmo in the airport, I’ll say, ‘I’m your huckleberry,’ but I wouldn’t say it to Bob Dylan.”

Afterward, he sent Dylan a recorded version of one of his songs to make up for it.

“I felt so bad about it. I was like, how could I make it up to him? So what I did was, I recorded ‘It’s Alright, Ma (I’m Only Bleeding)’ but as Doc Holliday, and I put in all of the big lines from the movie into the song and made him a little tape.”

The meeting may not have gone as poorly as Kilmer thought. Dylan later asked him to appear in his film Masked and Anonymous.

“I am a friend of Bob’s, as much as Bob has friends,” Kilmer told Esquire. “Bob is a funny guy. He is the funniest man I know.”

Even after they’d gotten to know each other well, Dylan continued to reference Tombstone every time he saw Kilmer. 

“Every time I run into Val Kilmer, I can’t help myself,” Dylan said in an interview with Bill Flanagan (via HuffPost). I say, ‘Why, Johnny Ringo — you look like somebody just walked on your grave.’ Val always says, ‘Bob, I’m not Johnny Ringo. That’s just a role I played in a movie.’ He could be right, he could be wrong. I think he’s wrong but he says it in such a sincere way. You have to think he thinks he’s right.”

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