Before Keith Gordon’s parents died, they spoke to him about the letters. “I had two deathbed requests from my parents,” he reveals to Closer. “My mom said, ‘Never get rid of the letters,’ and my dad said, ‘Please, whatever you do, get rid of the letters!’ So, I’ve always felt there was no way to win.”

Actor James Dean wrote those letters to Keith’s mother, New York actress Barbara Glenn, as his star began to rise. The couple, who had been introduced by actor Martin Landau, dated for two years but remained close even after the Rebel Without a Cause actor moved to California. “It was a weird mix of romance and friendship,” says Keith, who sold three of the letters through Christie’s in London in 2011 but held on to several others.

The letters confirm many of the characteristics ascribed to Jimmy, who died in a car crash in 1955 at age 24. “I got the sense from his letters that he was very obsessed with his work, his art and doing a good job,” Keith says. “He did not suffer fools gladly … but he had a really good sense of humor.”

It’s clear from his emotional correspondence that Jimmy was also quite lonely. “There were a lot of sweet things like ‘I miss you’ and ‘It’s so hard to be so far away,” Keith reveals. “He seemed like this intense, somewhat lonely and a little confused guy. You get a sense of the ups and downs [in their romance].”

James Dean in 'East of Eden'

In one letter, Jimmy unexpectedly chides Barbara for accepting a swimsuit modeling job. “He got really moralistic with my mom and said she was selling herself out cheap,” says Keith, describing what sounds like the ranting of a possessive boyfriend. “He decided she was prostituting herself, which is odd because they weren’t naked pictures. I found it so funny since they were all from this super-hip 1950s crowd.”

Keith didn’t hear much about his mother’s relationship with the iconic actor growing up. “It was this weird semi–family secret because my dad was super jealous,” Keith admits. And it’s hard to blame his father, actor and stage director Mark Gordon, for feeling that way. Barbara’s courtship with Jimmy was a milestone for her. “I think it was the love of her life,” he says. “She was a couple of years younger than him, and I think it was her first big romance.”

Before Jimmy’s untimely death, Barbara confessed to him that she had met Mark, the man she would marry. “In the last letter from Jimmy to my mom, he says that my dad was a good man,” Keith shares. “He said that what they had was too crazy and was never going to work. He was really happy that she was with someone who was stable and sane. He was sort of giving her his blessing.”

That’s the letter Keith, who became an actor and filmmaker himself, is least likely to part with. “It’s really sweet and personal,” he says. “And it’s one I like the most because it actually sort of connects to my own coming into existence!”