And when the script for Vice came along, Madsen knew he'd found the film he'd been looking for.
Madsen, who teams up with his Kill Bill co-star Daryl Hannah in the new movie, says, "Chris and I were very good friends and when he died it just shattered me. I was completely f**ked up for a long time. I couldn't believe he was dead.
"He was such a strong, wonderful guy. We had a lot of fun together over the years. I just miss him very much and thought it would be nice to dedicate the film to him, so that's why I did it."
The actor even tried to land Penn's mother a role in the movie: "I wanted his mother Eileen to play my mother in the film, but the casting people in Vancouver made sure that didn't happen. I see her around Malibu and go and visit her once in awhile. She's a lovely lady."
Source: WENN