The Incident (1967)
The Role: Artie Connors
Why It’s The Best: Sheen makes an arresting big screen debut as violent hoodlum Artie Connors, one of a pair of teen villains who board a New York subway train and proceed to terrorise the hapless passengers. Projecting a sneering malice that jars with his baby-faced looks, it’s a striking opening salvo from an exciting new talent.
Iconic Moment: The point when the mask finally slips, and Artie's tough-guy routine is replaced by cowering terror in the face of his partner’s increasing mania.
Sheen Says: “I came up in the James Dean era. He was the phenomenon of the day, taken away in 1955. I went to New York, to act, in 1959, and there was a belief then that if you were talented you would get your break.”
The Subject Was Roses (1968)
The Role: Timmy Cleary
Why It’s The Best: Sheen turns in a dazzling performance alongside the Oscar-winning Jack Albertson in this adaptation of the Pulitzer-winning play of the same name. He plays Timmy, a young man who returns from WW2 to find his apparently happy home life coming apart at the seams. Reprising the role he had played on stage to widespread critical acclaim, Sheen is right at home as the son caught between his feuding parents.
Iconic Moment: The crucial moment of realisation when it dawns on Timmy that he is to blame for the rift between his folks.
Sheen Says: “We’re all struggling with this basic need to know our worth. Love is so scarce, and this story focuses on that. If you don’t leave home with the true sanctity of being, you won’t see that sanctity in anyone else.”
The Role: 1st Lieutenant Dobbs
Why It’s The Best: It’s a relatively small part, but is worth flagging up on the grounds that Sheen’s bright-eyed decency more than holds its own amid a host of grandstanding performers. When you make your presence felt alongside Alan Arkin, Anthony Perkins, Charles Grodin, Jon Voight and Orson Welles, you know you’re doing something right.
Iconic Moment: Arkin and Sheen enjoy a fine rapport throughout the film, as evidenced by the following exchange: “If he raises the number of missions again, I swear to God, I'll help you kill him,” begins Arkin. “Really?” replies Sheen. “I swear,” is the response. “Well, that’s very reasonable of you,” concludes Sheen.
Sheen Says: “Going to Mexico was memorable. We just left a blizzard in New York City then we were in San Bernado desert, and the boys would bring home kids from the fishing village. I remember one night Ramone disappeared during this huge carnival. Here we are in a foreign country and I’ve lost one of my kids!”
The Role: Kit
Why It’s The Best: It’s the role that Sheen himself regards as his best work, and the one that marked his arrival as a major Hollywood player. Oozing an icy charisma as the James Dean obsessed Kit (Dean was an idol of Sheen’s also), he’s a disconcertingly magnetic screen presence, even when his bloodthirsty deeds threaten to turn the stomach. A towering performance in one of the greatest films of the ‘70s.
Iconic Moment: The scene in which Sheen and Sissy Spacek dance to Love Is Strange as it plays on their portable radio. This sequence sums up the film’s offbeat mood perfectly.
Sheen Says: “It was mesmerising. It disarmed you. It was a period piece, and yet of all time. It was extremely American, it caught the spirit of the people, of the culture, in a way that was immediately identifiable.”
The Little Girl Who Lives Down The Lane (1976)
The Role: Frank Hallet
Why It’s The Best: Sheen is unspeakably menacing as the sexual deviant with eyes for 13-year-old Jodie Foster. Even more disconcerting when viewed in contrast with Sheen’s cuddly later roles, it’s an uncomfortable performance to watch, and yet one you can’t tear yourself away from. Sheen may have been in better films, but he’s never been more frightening.
Iconic Moment: He tortures and kills poor Jodie’s pet hamster with a cigarette. Told you he was a nasty piece of work…
Sheen Says: Marty has always been fairly quiet on this one, but it’s no secret what Foster thought of the end product: “When people are there to simply do a job they don't have any passion for,” she says, “those are nearly always bad films.” We can’t agree with her in this case... it’s a scuzzy, cult thriller to be savoured!
Apocalypse Now (1979)
The Role: Captain Benjamin L Willard
Why It’s The Best: The role with which Sheen is most closely associated, and the one the man himself ranks alongside Badlands as his finest hour. Dead drunk throughout much of the shoot, and suffering a heart attack after 12 months of gruelling work, Sheen has often said he wouldn’t have taken the role had he known what was involved. Thankfully for us, he had no idea!
Iconic Moment: There are many to choose from, but we’ll go for the climactic scene where Willard slowly and deliberately makes his way into Kurtz’s chamber…
Sheen Says: “I brought to that part everything I was, wanted to be, wasn't. Francis saw my false self. He saw the gap between the real me and this macho guy, this worldly actor. That's what a great director does. And he said, ‘Get rid of the image, play the reality'. That's what he wanted, this lonely guy, completely isolated in himself. And that's what you saw.”
That Championship Season (1982)
The Role: Tom Daley
Why It’s The Best: Jason Miller’s adaptation of his own play paints an affecting picture of mid-life crisis, as a group of high-school basketball teammates meet up to reminisce on their glory days. Inevitably, it isn’t long before old resentments come to the surface, and tensions soon begin to flare. Sheen is excellent as the drifter with a drink problem, drawing on his own troubles with the bottle to conjure up a memorably tragic performance.
Iconic Moment: The scene in which Mitchum follows a drunken Sheen around the house, berating him for the way his life has gone off the rails. “And you,” he snarls, “stumbling and reeling through the streets like some broken thing, hearing people laugh at you… it breaks my heart. You were a gifted boy!” The expression of blank defeat on Sheen’s face is a picture.
Sheen Says: “I’ve often felt that acting was above all, good therapy!”
The Role: Vince Walker
Why It’s The Best: It’s only a small part, but Sheen makes the most of his limited screentime as journalist Vince Walker who meets and befriends Gandhi when covering his struggle for the newspaper. The easy chemistry between Sheen and Ben Kingsley feels convincing throughout, and whilst the character might be one of the few fictional figures in Richard Attenborough’s film, the role is legit: Gandhi was indeed befriended by a writer, an American journo named Webb Miller.
Iconic Moment: An understated back and forth that outlines what Gandhi is all about. “You’re an ambitious man, Mr. Gandhi,” says Walker. “I hope not,” replies his friend.
Sheen Says: “It was only five or six weeks. But it was enough to make a profound impression on me, because I had been in the third world before but never that type of third world. The poverty was unbelievable.”
The Dead Zone (1983)
The Role: Greg Stillson
Why It’s The Best: We’ll admit, we’re including this one largely because of the parallels with Sheen’s other political performance as Bartlet in The West Wing . Because whilst President Bartlet is a wise, benevolent statesman, Sheen’s character in The Dead Zone is a power-hungry maniac who can’t wait to get his hands on the nukes. OTT it may be, but there’s no doubting his performance is bloody good fun!
Iconic Moment: When Christopher Walken has a premonition of Stillson’s presidency, in which America’s new leader kicks off a nuclear war whilst practically foaming at the mouth. “You’re not the voice of the people,” he barks at a cowering general, “I am the voice of the people! They speak through me, not you! It came to me in the middle of the night… I must get up now, right now and fulfil my destiny! Now you put your goddamn hand on that scanning screen, or I’ll hack it off and put it on for you!”
Sheen Says: “I had a pretty in-depth knowledge of what went on with the characters behind the scenes at Watergate. I mean the whole world got a pretty good picture of what some desperate men in a desperate situation are willing to do, not dissimilar to the character I play in Dead Zone . But I don’t think any of those men were really as hideous or as sleazy as Greg Stillson who would stop literally at nothing to get to the White House."
Wall Street (1987)
The Role: Carl Fox
Why It’s The Best: Sheen is the onscreen father of offscreen son Charlie, playing him with the sort of blue-collar decency entirely missing from the amoral Gekko. Michael Douglas might get all the best lines but Sheen Sr is the film’s beating heart.
Iconic Moment: His despairing words of wisdom to the son he no longer recognises: “I don’t go to bed with no whore and I don’t wake up with no whore. That’s how I live with myself. I don’t know how you do it.” The sort of thing you could envisage Martin saying to Charlie off screen as well…
Sheen Says: “No father could ever be prouder of his son. I hold Charlie's accomplishments dearer than my own. He has been through so much and overcome so much more. Even if he weren't my son he'd still be my best friend.”
The Role: Otis V McKinney
Why It’s The Best: As well as taking on directorial duties, Sheen turns in a deliciously nasty performance as the bigoted officer in charge of a military prison largely made up of black inmates. Only troubled newcomer Charlie Sheen is willing to rebel against his reign of prejudice in one of the more notable Sheen family team-ups…
Iconic Moment: Okay, so it might be a bit nudge-nudge for some tastes but we love the meta-humour at work when McKinney tells his young rival that he himself has a son around his age.
Sheen Says: “If there is one guy who gets all the blame, it's the director. He doesn't always get all the credit if it's a success. It's too big a job.”
The Role: General Robert E Lee
Why It’s The Best: Sheen straps on a big old beard and fires his booming voice up to eleven in this grandstanding civil war drama. With plenty of stirring speeches to get stuck into, Sheen has rarely been more authoritative on the big screen, oozing passion and revolutionary zeal from every pore.
Iconic Moment: His impassioned speech to Tom Berenger: “We are prepared to lose some of us, but we are never prepared to lose all of us. And there is the great trap General. When you attack, you must hold nothing back. You must commit yourself totally. We are adrift here in a sea of blood and I want it to end. I want this to be the final battle.” Stirring stuff.
Sheen Says: “I don't have a personal interest in politics per se. I have a great interest in the issues that are publicly debated, but I have a far greater interest in social justice and peace.”
The American President (1995)
The Role: AJ MacInerney
Why It’s The Best: Sheen plays Chief Of Staff to Michael Douglas’ President in what could be mistaken for an extended audition tape for The West Wing . Sheen has long since proven his chemistry with writer Aaron Sorkin, and that spark is in evidence again here as Sheen sets about stealing the movie from under Douglas’ nose. When it comes to Oval Office-based shenanigans, he’s the best in the business.
Iconic Moment: His discreet disclosure of the privileges afforded to the American President: “Mr. President, this is election year,” he begins coyly, “If you're looking for female companionship, we can make certain arrangements that will ensure total privacy.” “I don’t want you to get me a girl, AJ,” snaps the President. “What is this, Vegas?” “No sir,” responds AJ placidly, “this is the White House.” If only he’d been around when Clinton was in…
Sheen Says: “I haven't done a big-budget studio film since American President and that was because Rob Reiner just insisted that I do it. He was just magnificent to me and I'm very grateful for it.”
Catch Me If You Can (2002)
The Role: Roger Strong
Why It’s The Best: Sheen taps into the gruff side of his persona as Amy Adams’ disapproving father Roger. A buttoned-up, emotionally repressed patriarch, Roger has disowned his daughter out of shame over her abortion, until her seemingly perfect boyfriend engineers a reconciliation. Sheen tones down the usual twinkle in his eye to present a cold and ultimately pitiful portrait of failed fatherhood.
Iconic Moment: The family dinner scene where a frosty Roger gives young Abagnale the third degree…
Sheen Says: “If you walked on the set, and didn't know what (Spielberg) looked like you wouldn't know who the director was. It's because he's so low key. He treats everyone the same. The cast and crew adore him easily and they'll do anything for him.”
The Departed (2006)
The Role: Captain Queenan
Why It’s The Best: As one of the few straight-shooting characters in a movie full of double-crossing wrongdoers, Sheen brings a pleasing dose of integrity to Scorsese’s twisty-turny crime drama. He has the look of a man who’s ready for his pension, which makes it all the more admirable when he puts himself out on a limb for DiCaprio’s undercover snitch.
Iconic Moment: He’s given plenty of meaty dialogue to chew on, but inevitably, the most memorable moment is when he unexpectedly does a header off a high-rise, splattering Leo with gore in the process.
Sheen Says: “The three of them (Matt Damon, Leo DiCaprio and Jack Nicholson) were a delight. I had one scene with Jack and I'm such a huge fan of his work. And they are so good-natured. They can't go from here to there without being mobbed.”
The Role: Jack
Why It’s The Best: A small role it might be, but as Bobby Kennedy’s campaign manager Jack, Sheen brings a welcome dose of gravitas to a cast heavily weighted with up-and-coming stars. Having played both John and Bobby Kennedy on TV, it seems only appropriate that Sheen should crop up here somewhere. And then there’s the fact that his son Emilio is the director…
Iconic Moment: His stunned reaction at the film’s close, part of a montage of similar shots featuring the rest of the film’s classy ensemble.
Sheen Says: (On the cast) “The names are just stunning. And there’s a lot of these young people I don’t know. You’d walk on set and everyone would say, ‘Miss (Heather) Graham is here,’ or, ‘Mr (Ashton) Kutcher is here.’ Everyone’s falling over them and I didn’t know who they are.”
The Way (2010)
The Role: Tom
Why It’s The Best: Sheen re-teams with son Emilio Estevez for this thoughtful, heartfelt road movie about a father’s pilgrimage to recover the body of his estranged son. Tapping into themes of Catholicism and referencing Sheen’s Spanish heritage, it’s clearly a deeply personal project for the director, and one that helps coax a powerful, haunting performance from his star.
Iconic Moment: The flashback to a message from his son (played, naturally, by Estevez) by which Sheen finally begins to understand his troubled offspring.
Sheen Says: “Everyone's seeking a transcendent experience. I think we all, for our own health, need to explore our inner journey and our inner life and we ask those questions: Who am I? Why am I here? And that's why we go on pilgrimage.”