Sean Penn and Harry Dean Stanton both appeared in the same Two and a Half Men episode with Charlie Sheen, but Stanton's acting really stood out.
When Harry Dean Stanton died in 2017, many people shared a clip of him on Two And A Half Men. Stanton guest-starred on the season 2 premiere of the comedy, making a memorable appearance in Charlie's support group. He appears alongside Sean Penn, Bobby Cooper, and Elvis Costello.
While Sean Penn is the high profile guest star in Two and a Half Men season 2, episode 1, Stanton steals the scene with his long tangents about the meaning of words. He memorably told Charlie, "Let me tell you something about... 'relevant.' The root of the word 'relevant' is 'rel,' which is also the root of the word 'relative.' Your brother is your 'relative,' ergo, your brother is 'relevant.'" The line shouldn't be funny, but Stanton's delivery makes the explanation one of the funniest monologues in Two and a Half Men's history
In the episode, Alan learns that Charlie is a member of an exclusive group for men and is desperate to join. When Charlie doesn't let Alan join them, he tries to get in touch with his old friend. Alan soon learns his ex-wife, Judith, has turned them against him.
When Alan is finally allowed in the famous group, he is so irritating he ends up getting himself tied to a streetlamp.
Sean Penn's Relationship With Harry Dean Stanton
Sean Penn and Harry Dean Stanton's relationship began way before they appeared in the same Two and a Half Men episode. When Sean Penn was a rising star, he admired Harry Dean Stanton so much he followed him to Cannes and stayed in the actor's hotel room for five days.
Stanton, who was promoting 1984's Paris Texas, was incredibly nervous about going to the film festival. Director Wim Wenders recalls that "he was full of self-doubt, and we had to hold his hands every evening,"
To ease Stanton's nerves, Wenders encouraged the Alien actor to bring an assistant. "I said: 'Find somebody who can help you and who can be with you, and whatever you need, he can let us know."
Wenders added, "And Harry brought an assistant. Not many people know that. A young actor who was there all the time, who helped Harry get into his tuxedo; he was really comforting him, and he was there strictly for Harry and very modestly so. And the young actor was called Sean Penn."
Stanton would collaborate with Penn as a co-star in the films She’s So Lovely and The Pledge, as well as an episode of Two and a Half Men. In his obituary, Sean Penn called Stanton "a man’s man." And added that the late actor was "one of the gentlest, kindest, most ornery and philosophical, old b****** any of us ever knew. There was something perfect about Harry Dean."
Harry Dean Stanton's Previous Roles With Two And A Half Men's Charlie Sheen And Jon Cryer
Just like Sean Penn and Harry Dean Stanton, Harry Dean Stanton has also had a relationship with both Charlie Sheen and Jon Cryer before joining them on Two and a Half Men.
Stanton has appeared in more than 100 films since his debut in 1956, including that unforgettable Two and a Half Men guest spot. His most notable recent lead was in the hit HBO series Big Love, playing Roman Grant, the morally questionable head of a religious compound. His other significant movies include Lucky, Repo Man and Alien.
Before appearing together in Two and a Half Men, Jon Cryer starred alongside Harry Dean Stanton in Pretty in Pink. Cryer wrote a touching story about meeting Stanton, after he passed at 91 years old.
"One of the most lovely, surreal moments I've ever had in Hollywood was the night I went to a party that had a country band sort of twanging away in the corner. At one point this ghostly, gorgeous voice cut through the din. I turned to see Harry Dean Stanton on the tiny stage playing with the band," Cryer told ET.
"I'd come to know Harry as an incomparable character actor with a grizzled seen-it-all demeanor. But I was unprepared for his beautiful, affecting singing voice. It was the very definition of soulful. And I suppose I'll feel a little better knowing that soul has found peace. Rest In Peace Harry.”
Charlie Sheen, who shared the screen with Stanton on Red Dawn, as well as the season 2 episode of Two and a Half Men, also celebrated the late actor.
"Harry Dean Stanton, brilliantly and effortlessly, played my father twice and my Sage once. All the while, in between and often, he played with our collective hearts and imaginations, in methods unworthy of this scribe's deciphering," Sheen wrote in a statement at the time.
Charlie Sheen's Childhood Connection To Sean Penn
Charlie Sheen and Sean Penn's friendship was not just for the hit sitcom. The pair had been friends in high-school and often made 8mm movies together. The pair also went to school with Rob Lowe, Robert Downey Jr. and Sheen's younger brother, Emilio Estevez. Penn, a director himself, has credited his time making movies with his childhood friends as helping him in the industry.
Sheen has praised Sean Penn for his ability to party, calling the actor, alongside Johnny Depp, as one of the most prolific partiers he knows. "Sean [Penn] is hardcore. Sean is hard to keep up with when he's going. And he's gnarly. He's the best actor alive."
The Milk actor praised the Two and a Half Men star, even during Sheen's very public controversies. “Charlie is one of the very few public people who cannot be accused of using the media to his own benefit."
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