Jimmy Stewart 101: Your Guide to the Great Actor’s Most Pivotal Roles

Whether playing affable idealists or obsessed lovers, Hollywood’s finest everyman was a master of subtlety and empathy

Technically, his name was James Stewart, but anyone so affable and self-deprecating just felt more like a Jimmy. Where other actors of his era seem towering — Humphrey Bogart, John Wayne, Cary Grant — this small-town Oscar-winner was always human-scaled, which was a large part of his appeal. Stewart, who died in 1997 at the age of 89, didn’t have to fake it to play everymen, and his embodiment of what constituted a good, decent American remains comforting and aspirational. He fought in World War II but never wanted his military service used as part of the promotion for any of his pictures. He praised his fellow actors and avoided the tabloids. By all accounts, he was a standup gent. “I’d like to be remembered as a man who believed in hard work and decent values,” Stewart once said, “as one who believed in the love of country, love of family, love of community, love of God.”

If that makes him sound corny or square, it also engendered the deep affection that fans have harbored for him for generations. Some of his best films are about idealism in the face of cruelty and cynicism, and Stewart sold viewers on the power of optimism as much as any movie star ever has. But he also underwent a remarkable onscreen transformation, morphing from a young, handsome romantic lead into a middle-aged actor who was able to articulate his complicated characters’ darkest obsessions. Because the world first got to know Stewart as the aw-shucks charmer, it was even more shocked and moved by the range and depth he’d eventually reveal.

Still, it’s easy to typecast this soft-spoken Midwesterner with the distinctive drawl. Any comic worth his salt did a Jimmy Stewart impression — lots of stammering and extended vowels — that reduced him to a simpleton, but his performances were too full of fire, too charged up by his characters’ belief in their dreams, for the caricature to stick. The closest modern-day analog we have is Tom Hanks, who too has figured out how to make decency and nobility compelling while hinting at the storm clouds just on the horizon.

Want to know where to start with Stewart’s formidable body of work? I’ve selected 10 essential films and, admittedly, many are no-brainers. But there’s no point in being cute when handpicking the man’s highlights. The classics are classics for a reason, and even better, they still hold up, illustrating why he’s never gone out of fashion. Terrific romantic comedies, dark psychological thrillers, stirring political fables, mythic Westerns: He was the everyman who could do everything.

Mr. Smith Goes to Washington (1939)

Stewart’s second collaboration with Oscar-winning director Frank Capra, after You Can’t Take It With You, remains the movie most Americans associate with the good ol’ days of our democracy, when a passionate idealist could fight for the little man and Congress would do the right thing. Sure, Mr. Smith Goes to Washington is pure fantasy, telling the story of an honest young man (Stewart) who’s roped into serving out a deceased senator’s term, unaware that the party bosses expect him to keep his mouth shut and follow orders. But the 31-year-old actor so beautifully expressed the character’s decency that no one ever doubted his ability to inspire legislators with his fiery words. 

The film earned Stewart his first Oscar nomination, but it also cemented his hero-of-the-downtrodden status, which he’d amplify (and sometimes subvert) for the rest of his career. As one critic at the time put it, “One can only hope that after this success, Mr. Stewart in Hollywood will remain as uncorruptible [sic] as Mr. Smith in Washington.” Few actors engendered such faith from audiences. We believed Stewart’s characters were as good as he seemed to be.

The Shop Around the Corner (1940)

Arriving just two months after Mr. Smith Goes to Washington, this sparkling Ernst Lubitsch comedy proved that Stewart could also be a supremely lovable romantic lead. He’s Alfred, who works at a quaint gift shop and cannot stand the new shopgirl, Klara (Margaret Sullavan), who despises him right back. Joke’s on them, though: They have a lively rapport as each other’s secret penpal, having no idea about their correspondent’s real identity. 

A couple generations later, The Shop Around the Corner would serve as the inspiration for You’ve Got Mail, and no surprise that our current Jimmy Stewart, Tom Hanks, starred in the remake. But it couldn’t hold a candle to the chemistry shown by Stewart and Sullavan. Boyish but witty, Alfred is the template for the handsome, charming bachelors he’d play throughout his career. (In real life, Stewart didn’t get married until his early 40s.) But, remarkably, this wasn’t even his best film (or performance) from 1940.

The Philadelphia Story (1940)

Based on the hit play, The Philadelphia Story is an excellent romantic comedy featuring three winning leads: Katharine Hepburn played Tracy, a socialite who’s about to remarry; Cary Grant was Dexter, her ex-husband determined to win her back; and Stewart tackled the role of Mike, a journalist assigned to cover the big gala. Plenty of other actors considered signing up for the film, but now it’s impossible to imagine anyone but those three in those roles. 

Initially, however, Stewart didn’t figure he’d be in the running. “When I first read the script,” he once said, “I thought I was being considered for that fellow engaged to Hepburn. But as I read it, I thought to myself, ‘Ooh, that reporter part is a good one, I’ll be happy to play it.’” Turns out, he’s a perfect Mike, falling for Tracy and proving to be a worthy adversary to the more suave Dexter. 

For years, fans of The Philadelphia Story have debated whether Tracy ended up with the right guy, but the Academy Awards definitely made the correct choice, honoring Stewart with Best Actor — his only competitive Oscar. Not that Stewart necessarily agreed with the Academy’s choice: He’d voted for his dear friend Henry Fonda, the star of The Grapes of Wrath. Later reflecting on his win, Stewart once said, with typical humility, “I guess people just think I’m good at playing newspapermen.” 

It’s a Wonderful Life (1946)

Capra pitched an idea to Stewart about a guy in a small town who marries his sweetheart, has a family, becomes disillusioned, considers suicide but then meets an angel. During the pitch, though, the director worried that the story sounded terrible. Stewart replied, “Frank, if you want me to be in a picture about a guy that wants to kill himself and an angel comes down … when do we start?” Such was the actor’s faith in his Mr. Smith collaborator that he signed up for It’s a Wonderful Life, a Christmas staple that’s actually far more despairing than you remember.

As George Bailey, Stewart personified a type of postwar American male who realizes that his homeland isn’t quite the land of opportunity but, rather, a place where greed and small-mindedness flourish. As such, It’s a Wonderful Life is a nice pairing with Mr. Smith, with an older, wiser Stewart playing a man whose idealism has almost been beaten out of him. What makes the movie so poignant, however, is that George will find out, yes, he has lived a good life — even though he considered himself a failure. Despite It’s a Wonderful Life’s yuletide theme, it’s often pretty bittersweet — and a hint of the darker movies Stewart would soon start exploring.

Still, it’s possible this is still the film he’s most associated with. Stewart understood that: When he received an Honorary Oscar in 1985, he closed his acceptance speech by thanking “the audience, all you wonderful folks out there. Thank you for being so kind to me over the years. You’ve given me a wonderful life.”

Harvey (1950)

Before it was a film, Harvey was an acclaimed Broadway play, which was where Stewart first portrayed Elwood, a good-natured drunk whose best friend is a rabbit no one else can see. The movie earned him an Oscar nomination, which was a tribute to the actor’s seemingly inexhaustible ability to get audiences on his side. To be sure, Harvey is a simplistic paean to optimism — it’s a precursor to films like Forrest Gump, which also value cheerfulness over cynicism — but Stewart embodies that guilelessness so effortlessly and convincingly that you never doubt Elwood’s sincerity. He may be an alcoholic and a fool, but he’s not crazy, which is what a lot of the people around him in this movie think.

Stewart’s longtime friend Henry Fonda would talk about his pal’s belief that the original play (which won a Pulitzer) was better than the movie, adding, “But I tell you this: when Jim plays Harvey on stage or on film, nobody can play the part better.” And much later in life when Stewart’s film career started to fizzle out, he returned to the comfort of Harvey, reprising his role as Elwood in a London production in the mid-1970s. “I don’t think I’ll be making any more movies,” he said at the time. “I just don’t fit in. I just get bewildered by some of the scripts that still get sent to me. … Right now, I’m just enjoying playing Harvey.” 

The Naked Spur (1953)

Of Stewart’s frequent collaborators, director Anthony Mann doesn’t get nearly enough credit. The two men made eight films together, and the actor was eternally appreciative to the filmmaker for helping him during a rough patch professionally. “After I came back from the service in 1945,” Stewart recalled, “I had trouble getting my career going again. I wasn’t under contract to any studio, and I made about seven pictures that just didn’t go. Then somebody introduced me to Mann.” 

Principally, they did Westerns, and the best of the bunch, with all due respect to Winchester ‘73 and The Man From Laramie, is this intense psychological study, in which Stewart plays Kemp, who returns from the Civil War to learn he’s lost his home and that his wife has abandoned him. Reduced to being a bounty hunter, Kemp marked a period in which Stewart consciously took on less lovable roles, and the character’s mental collapse signaled the heights he was about to reach. Beaten down by the war and the personal traumas he’s faced, Kemp is ostensibly the hero, but The Naked Spur never leaves us too confident about that fact. The film builds to a moving finale that only works because we absolutely believe what a sonofabitch Stewart’s character could be up to that point.

Rear Window (1954)

“The wonderful thing about it is that so much of it is visual,” Stewart said in 1983 about Rear Window. “You really have to keep your eye open in the film, because it’s a complicated thing. And the audience was really with it, I thought that was just amazing. It just bears out the feeling that so many of us had about Hitch and his way of doing things.”

“Hitch” was Alfred Hitchcock, and this 1954 gem was their second pairing, after Rope, which wasn’t nearly as successful. Beyond being arguably the greatest film ever made about voyeurism — about the primal pleasure of moviegoing itself — Rear Window remains a nifty thriller, telling the story of hobbled photographer Jeff (Stewart) who starts taking an interest in the people in the apartment building across the street, eventually believing that one of the residents may have been murdered. 

By this point, Stewart had shed some of the Mr. Smith sweetness, and indeed his Rear Window character is a bit of a bastard, ignoring his kind, beautiful girlfriend’s (Grace Kelly) very sensible request that they get married because he doesn’t want to be chained down. (In many ways, the story’s mystery plot is just Jeff’s way of avoiding his immature commitment issues.) As always, Hitchcock ratchets up the tension terrifically, but Stewart’s prickly performance adds an extra layer of complexity to a story about the allure and danger of escapism.

Vertigo (1958)

Every 10 years, the prestigious film journal Sight & Sound polls the world’s preeminent critics to pick the greatest movies ever made. In 2012, Vertigo topped the list — it was the first time since 1952 that Citizen Kane wasn’t at No. 1 — and that honor speaks to the deep respect cinephiles have for Stewart’s layered, disturbing performance. 

Once again working with Hitchcock, he’s Scottie, a San Francisco detective who falls in love with a woman, Madeleine (Kim Novak), that he’s supposed to be trailing. When she dies tragically, Scottie is bereft — until he meets another woman, Judy (also Novak), who looks just like her.

This psychological thriller can be interpreted different ways — for one thing, it’s a movie about Hitchcock’s desire to control his leading ladies — but it’s the apex of Stewart’s transition from Endearing Everyman to Troubled Obsessive. Scottie starts off as a sympathetic, likable gumshoe, but he devolves into a monster once he tries to remake Judy into his dead love. The decency that Stewart always conveyed on screen here is used to suggest how a good man can become so bad.

Stewart once explained that he was drawn to characters who “it is an effort to get along with in real life, whose judgment is not always too good and who makes mistakes. I think human frailty is a very nice thing to portray.” Vertigo was human frailty teetering into madness, and it’s Stewart’s finest film work.

Anatomy of a Murder (1959)

One of the great courtroom dramas, this Otto Preminger film strips away the theatrics you usually see in these movies, giving us just a smart, absorbing story of a defense attorney (Stewart) trying to help his client (Ben Gazzara) beat a murder rap, even though the guy absolutely did it. (He says he killed because the victim raped his wife.) And so what follows is a fascinating study of how Stewart’s lawyer fights to keep the man out of jail, brilliantly matching wits with George C. Scott’s sharp prosecutor.

Gazzara was in awe of Stewart’s dedication to playing this complicated character, a former big shot who wants one last win. “He closeted himself, because he had a great deal of dialogue,” the younger actor recalled. “I never even saw him take lunch, actually. I think he did that alone, totally concentrated on this character, totally immersed in it.”

Anatomy of a Murder earned Stewart his final Oscar nomination, but he lost to Charlton Heston and Ben-Hur, which dominated the 1960 Academy Awards. Nonetheless, it’s a film hailed for its provocative subject matter — rape wasn’t something freely discussed in Hollywood movies of the time — and its intelligent, gripping look at the legal system. Plus, Anatomy of a Murder was a fitting finale to Stewart’s most adventurous decade of film acting. 

The Man Who Shot Liberty Valance (1962)

Stewart was 54 when this melancholy, barbed Western opened in theaters, casting him alongside John Wayne in one of the genre’s finest offerings. He’s Stoddard, a revered U.S. senator who’s returned to his hometown for the funeral of a seeming nobody, a cowboy named Doniphon (Wayne). The Man Who Shot Liberty Valance tells its story through flashbacks, showing how Stoddard built his early reputation on being the man who killed the deadly outlaw Liberty Valance (Lee Marvin) — except, maybe he wasn’t the guy who actually pulled the trigger.

This John Ford opus is one of the key revisionist Westerns, part of a series of films that peeled back the conventions to question the one-dimensional heroism these movies usually contained. In this way, Stewart was an ideal choice to play the obvious Jimmy Stewart character — a brave everyman who stood up to evil. Consequently, The Man Who Shot Liberty Valance subverts our expectations, resulting in a wry commentary on all the ostensibly good guys this beloved actor played.

The film was dismissed at the time but has gone on to be considered a classic. Still, The Man Who Shot Liberty Valance was Stewart’s final major film. After that, he was part of the Oscar-winning How the West Was Won, which also came out in 1962, but he never quite captured the public’s imagination again. No matter: He’d earned more than enough of a legacy by that point to fade gracefully from the limelight.

“The Hollywood product today places too much emphasis on shock and not enough on old-fashioned sentiment,” he said in the mid-1960s. “I still like to do movies that make the ladies cry.” 

Corny and square to the end, Stewart was wrong in only one regard: It wasn’t just female viewers who were moved by his exemplary work.