Jimmy Stewart may have appeared the charming boy-next-door, but his Westerns reveal a darker side. His cowboys were often men of questionable character, battling private demons and fleeing violent pasts. They eventually proved their heroism, of course, but not before leaving the audience in serious doubt. Intrigued? Read on for a list of the actor's finest work in the genre, ranging from a walk-on role as Wyatt Earp to a goofy starring turn as a sheriff who's not allowed to carry a gun.

The Rare Breed (1966)
While most cowboy movies stop at the cattle drive, here we enter territory that's off the map for most Westerns: The cutthroat world of cattle breeding! The Rare Breed stars Stewart as a cowboy charged with transporting a prize English Hereford bull to Texas where it will make hay with Lone Star stock. As is often the case with bovine romance, a group of ne'er-do-wells will stop at nothing to prevent this beautiful transcontinental love affair from taking place.

Shenandoah (1965)
The trope of the peaceful man pushed into violence is a common one in the Western, and here Stewart plays a wealthy Virginian who would like to be as neutral as Sweden. But when he's son gets kidnapped by the Confederacy, all bets are off! And for a man who believes that it's not "his" war to fight -- as many Americans felt about the Vietnam War at the time the movie was made -- it turns out he has plenty to lose.

Cheyenne Autumn (1964)
Playful cinematic self-referencing didn't start with Pulp Fiction. In this John Ford flick, Stewart has a great walk-on as Wyatt Earp (most famously played by Henry in John Ford's My Darling Clementine), with Stewart's former nemesis in Bend of the River, Arthur Kennedy, playing his compadre Doc Holliday.

Two Rode Together (1961)
Once more Stewart offers up another dose of his particular brand of jaded charm. In a perfect case of against-type casting, Stewart is given the role of a corrupt sheriff while Richard Widmark (who's played his share of disreputables) accepts duties as an honest, idealistic calvaryman. Together, they band together to ransom kidnapped whites from Comanches -- albeit for very different reasons.

The Man Who Shot Liberty Valance (1962)
Many fans call this Ford's masterpiece and while The Searchers ranks a close second, it's hard to disagree. Liberty Valance explores the fragile line between truth and fiction with Stewart as a big-city lawyer who becomes a hero through something more powerful than simple violence: A lie. This one should be required viewing for anyone who claims to be a fan of Westerns, or of Stewart himself.

The Far Country (1954)
Stewart plays his most unsympathetic character yet in The Far Country. All Stewart's Jeff Webster wants to do is sell beef at inflated prices to prospectors in the Yukon. Unfortunately, he's stopped in his tracks by a sheriff who's even more unprincipled than he is! With his herd swiped, Webster fights the sheriff using every dirty trick in the book. While such generalized malice might have sunk the film with any other actor, Stewart's likability keeps things afloat.

The Naked Spur (1953)
Stewart's principal collaborator after the war was director Anthony Mann. Along with Ford and Wayne, Budd Boetticher and Randolph Scott, it's one of the great movie partnerships in the Western. And it doesn't get much better than The Naked Spur, in which Stewart plays a Civil War veteran turned bounty hunter who has his sites set on an elusive fugitive. The setup is conventional but, as with many of Mann's work, it merely sets the stage to spin one of the Wild West's most intense psychodramas.

Bend of the River (1952)
In his second collaboration with director Anthony Mann, Stewart plays another man with a troubled past: a reformed border-raider who make the bad choice of linking up with an old cohort (Arthur Kennedy) to guide a wagon train to Oregon. While Stewart may have turned over a new leaf, Kennedy has trouble seeing the light when an opportunity to profit comes along. As you can imagine, Stewart doesn't remain outside the fray for long.

Winchester '73 (1950)
Anthony Mann started out making film noir, and his training comes through in Winchester '73, Stewart's first picture with the director. An unconventional Western by any definition, the story begins with Stewart intent on slaying a murderer and using the eponymous rifle as bait. We follow as the firearm passes from hand to hand before returning back to Stewart, a gimmick that would later inspire the short-lived Robert Altman series Gun.

Destry Rides Again (1939)
By now you're probably hankering for lighter fare. This Western comedy is just the thing! Here Stewart plays Thomas Jefferson Destry, a lawman who once brought order to rough-and-rowdy Tombstone and is hired on to clean up another lawless town. The fact that Destry doesn't carry a gun makes him the subject of much lampooning. But the joke's on the outlaws as Destry proves time and again.

Click here for a full schedule of The Rare Breed on AMC.