Jimmy Stewart won the hearts of audiences everywhere with his “aw shucks” charm, making him one of the most popular Hollywood actors of all time. With a career spanning decades, Stewart represented an entire American generation. But sadly, Stewart didn’t always live a charmed life. Haunted by trauma and tragedy, few know that his secrets had the power to destroy him.
1. He Was A Loner
In many ways, Jimmy Stewart had the ideal American home life. Born James Maitland Stewart in Pennsylvania, Stewart’s father ran the family hardware store while his mother was an accomplished pianist. Although he’d one day grow to be one of Hollywood’s greatest stars, young Jimmy was a shy and reserved child and spent a lot of his time alone.
Oblivious to his own destiny, he harbored dreams that had nothing to do with acting.
2. He Didn’t Want To Be An Actor
Considering his beloved awkwardness, it’s not hard to imagine Jimmy Stewart holed up in a basement, working on his model airplanes, drawing, and thinking about a career in aviation. At this point, there was nothing that made him stand out from the crowd: He had middling grades, and teachers often caught him with his head in the clouds. Still, he did have one secret talent.
3. He Had A Secret Talent
Jimmy Stewart had a deep love for music and could play the accordion. One day at his father’s hardware store, a customer didn’t have enough money to pay for his items, so the man traded in his accordion instead. In a scene that could be from It’s a Wonderful Life, the local barber then taught Stewart how to play the instrument.
With his interests bouncing all over the place, the trajectory of Stewart’s future seemed treacherous…that is, until he had no choice but to straighten up.
4. He Abandoned A Dream
Though Stewart had dreams of becoming a pilot, his father had much bigger plans for him: Princeton University. Always a dutiful son, Stewart realized his father’s wishes and enrolled in the Ivy League university in 1928. Upon graduation, the college awarded him a hefty scholarship for his graduate studies—but instead of continuing his education, he made a shocking decision.
5. He Followed His Heart
After dedicating years to Princeton, Jimmy Stewart decided to follow his heart and joined a theater company, University Players. It was here that he met none other than Henry Fonda and Margaret Sullavan. Together, these three became the closest of friends, but it was so much more than that. Unbeknownst to Stewart, this was the beginning of one of Hollywood’s most epic love triangles.
6. He Had A Huge Crush
You see, while Jimmy Stewart became best friends with Henry Fonda, he also started to catch feelings for the lovely Margaret Sullavan. Finally, he decided to lay it all on the line and plucked up the courage to ask her out. Later, she described his proposition with the utmost warmth, calling it the “longest, slowest, shyest, but most sincere” proposition she’d ever received.
Unfortunately, their love never had the chance to take flight.
7. He Was A Womanizer
Although they were great friends, Stewart and Sullavan were never meant to be lovers…or, at the very least, their timing was never right. Both of them had sordid reputations: Stewart was a bit of a womanizer while Sullavan herself was quite the seductress. However, as we’ll see, destiny tied them together in the most heartbreaking way imaginable.
8. He Lost Her
For Stewart, Sullavan might just have been the one that got away. After she rejected him, the third member of their merry troupe, Henry Fonda, swooped in and stole Sullavan’s heart. Fonda and Sullavan married in 1931, but her adoration for Stewart never ceased. She wholeheartedly believed that Stewart was bound to be a huge Hollywood star.
In fact, this bittersweet friendship would later become the key to Stewart’s success.
9. He Had A Helping Hand
By 1936, Jimmy Stewart had landed a contract with MGM, but unfortunately, his B-movie roles left much to be desired. Meanwhile, his unrequited love, Sullavan, dominated the acting scene under Universal Pictures. Luckily for Stewart, she was determined to bring him with her. But this was no easy feat: His road to stardom had its fair share of struggle.
10. He Was A Nobody
When Sullavan read the script for Next Time We Love, she thought that it would be the perfect fit for Jimmy Stewart. There was only one problem, however. Nobody at Universal had ever heard of him. Thankfully, because of her insistence, they agreed to give him a screen test for the role of her leading man. After all of Sullavan’s efforts, Stewart won the part.
However, when he stepped onto set, a host of challenges flew at him from every angle.
11. He Was Too Nervous
At this time, Stewart lacked the confidence of a seasoned professional. Young and inexperienced, he felt wildly intimidated by this big production—and it was painfully obvious. He was a bundle of nerves, and before long, even the director, Edward H. Griffith, started to cruelly jab at his awkwardness in front of the camera. In fact, Griffith went straight to Sullavan and horribly insulted Stewart.
12. He Was A Joke On Set
Frustrated by Stewart’s nervousness, Griffith complained to the very woman who had vied for his casting. He told Sullavan, “Maggie, he’s wet behind the ears. He’s going to make a mess of things.” In her eyes, however, Sullavan had no doubts about Stewart’s capabilities. Stubborn to the very end, she devoted herself to mentoring him on her own time—and it led to unbelievable results.
13. He Transformed
Determined to get up to speed, Stewart agreed to spend his evenings with Sullavan. Open to her coaching, he started to rein in his bumbling mannerisms, although they eventually became one of his most beloved characteristics. She smoothed him out, and the results of her hard work impressed the director. In fact, after seeing Stewart’s transformation, he changed his tune entirely.
14. He Was Unrecognizable
Griffith later proclaimed, “It was Margaret Sullavan who made James Stewart a star.” And he wasn’t the only one shocked by Stewart’s newfound abilities. MGM’s Bill Grady was on the very same page, stating, “That boy came back from Universal so changed I hardly recognized him.” But as exciting as this was, all the time Stewart spent alone with Sullavan sparked some very scandalous rumors.
15. He Sparked Scandalous Gossip
Because of their nighttime rendezvous, gossip began to swirl about a potential affair between Stewart and his devoted teacher. It was all the more sordid considering Sullavan’s marriage to her second husband, William Wyler. He became increasingly suspicious about her stolen moments with Stewart. In the coming years, however, Stewart began to fuel the fire even more.
16. He Fueled The Fire
In 1936, Sullavan married again…but alas, it wasn’t to her stalwart pal, Jimmy Stewart. Still, many raised their eyebrows when Stewart coincidentally moved into a colonial home just around the block from her. Everyone was absolutely convinced of Stewart’s forbidden love for the actress. And based on his constant visits, they may have been right.
However, although Stewart kept his affection for Sullavan safely tucked into his back pocket, he kept looking forward. After all, Hollywood was a land of pleasure.
17. He Pursued A Dancing Legend
While Stewart stewed in his feelings of unrequited love for Sullavan for years, it was her first husband, Henry Fonda, who introduced him to his first real Hollywood fling. In 1935, Stewart kicked off his infamous bachelorhood with a brief romance with the dancing legend, Ginger Rogers. But although their love affair was brief, it marked one of his most intimate milestones.
18. He Gave Her Everything
Jimmy Stewart and Ginger Rogers had undeniable chemistry, and you can see it firsthand in 1938’s Vivacious Lady. Stewart, in his effortless way, conveys his lust for his co-star with his tender looks and bumbling banter. Behind the scenes, however, the two of them entertained a very passionate romance. And the cherry on top? It was actually Rogers who took Stewart’s virginity.
But while Rogers and Stewart broke new ground, his next film returned him to Margaret Sullavan’s magnetic orbit.
19. Their Chemistry Sizzled
Stewart and Sullavan were a winning pair. Fate brought them together once again in 1938 for their second film, The Shopworn Angel. Again, their acting harmonized perfectly. So much so, that even the powerful mogul Louis B. Mayer commented on the pair: “Why, they’re red-hot when they get in front of a camera. I don’t know what the hell it is, but it sure jumps off the screen.” Oh, but that wasn’t all.
20. He Wore His Heart On His Sleeve
You see, The Shopworn Angel’s plot had a love triangle that included actor Walter Pidgeon. While playing opposite Stewart and Sullavan, he came to a startling conclusion: He was the odd man out. The passion play centered on the two “friends” turned romantic leads. He remembered, “It was so obvious he was in love with her. He came absolutely alive in his scenes with her, playing with a conviction and a sincerity I never knew him to summon away from her.”
However, barred from making this relationship reality, Stewart looked elsewhere—and he certainly had options.
21. He Dated Huge Stars
Yes, Jimmy Stewart may have dominated romantic comedies as the prevailing “nice guy”—but off-screen, he was quite the bachelor. While making eyes at Sullavan during the production of The Shopworn Angel, he was also dating a heavy-hitter when the lights went down: For six whole weeks, he and Norma Shearer shared a fiery interlude.
When that diversion ended, Stewart didn’t have to worry: There was another beauty waiting in the wings.
22. He Broke Her Heart
Loretta Young was one of Hollywood’s most pious “good girls”—gorgeous and upstanding in every way. But while Young fell head over heels for Stewart, it became painfully clear that Young’s feeling far outweighed her beau’s. As such, he was on the fast track to breaking the poor girl’s heart. Down the line, Young’s daughter revealed the depth of her mother’s disappointment: “She wanted Jimmy to ask her to marry her and he never did.”
Unsurprisingly, Stewart wasn’t ready to settle down quite yet. After all, the life of a bachelor offered endless opportunities for fun…and trouble.
23. He Slept With A Married Woman
The next gal on Jimmy Stewart’s growing list of leading ladies was none other than Marlene Dietrich—a tryst made all the more naughty by the fact that she was a married woman. Together, they embarked on an affair during the filming of 1939’s Destry Rides Again—but their passion came to a sobering halt once Dietrich made a stunning announcement.
24. He Didn’t Want The Baby
When Marlene Dietrich told Stewart that she was pregnant, he was not happy. In fact, he made it clear that he wanted her to get an abortion, and after that, the relationship never stood a chance. She went ahead and terminated the pregnancy, but the damage was already done. Once filming wrapped, Stewart cut ties once and for all, pulverizing Dietrich’s heart in the process. And that wasn’t all.
25. He Was A Heartbreaker
Down the road, Dietrich expressed her feelings for Stewart in the most passive-aggressive way possible. When she published her memoir, she made sure to gloss over their relationship. Dietrich brutally framed Stewart as just a meaningless affair and mentioned him as little as possible. Clearly, Stewart had become quite the heartbreaker by 1940.
However, while his romantic life screamed its tumult, his professional career turned positively meteoric.
26. He Did It First
1940 was an amazing year for Stewart. For one, he got to reunite with his number one leading lady, Margaret Sullavan, on two projects—one being The Shop Around the Corner. The film would go on to inspire the classic 90s romcom, You’ve Got Mail, but let us not forget that it was Stewart and Sullavan who won over audiences with their chemistry long before Tom Hanks and Meg Ryan.
However, the project that truly made 1940 a standout year for Stewart took his fame to new heights.
27. He Was A Comedian
Stewart absolutely shone in the romantic comedy The Philadelphia Story, playing opposite Hollywood giants Cary Grant and Katharine Hepburn. Critics especially appreciated his comedy, and the film became a huge box-office success. But the rave reviews didn’t end there. One writer said that it was Stewart who “contributes some of the most irresistible romantic moments.”
But while he seemed the picture of confidence on screen, Stewart faced some distinct challenges throughout filming.
28. He Feared Failure
Stewart’s anxiety reared its head on the set of The Philadelphia Story—and there was one scene in particular that freaked him right out. The script called for a moment where Stewart’s character recites poetry to Hepburn. For some reason, he convinced himself that he’d fail. Luckily, actor Noël Coward came to the rescue and gave the worried actor some much-needed encouragement.
Nerves or not, Stewart overcame his doubts and went on to win his greatest accolade yet.
29. He Felt Undeserving
The Academy nominated both Jimmy Stewart and his old roomie, Henry Fonda, for Best Actor, but it was Stewart who took home the golden statue for The Philadelphia Story. The night was a triumph—except for one little thing. When they called his name, Stewart was pretty disappointed that he beat out Fonda for a surprising reason.
30. He Was A Fairweather Friend
Stewart sincerely believed that he didn’t deserve the award. Ever the altruistic friend, Stewart had actually voted for Fonda. After all, he’d been a supporting actor, not the lead. However, the confused winner had a hunch: He wondered whether this was the Academy’s way of mending the past year’s mistake when they’d failed to give him an Oscar for his excellent performance in Mr. Smith Goes To Washington.
But these worries were soon to be a thing of the past. With the end of the decade creeping up on him, Stewart had no clue that he’d soon be leaving Hollywood far behind.
31. He Had A Proposal Gone Wrong
Right before the nightmare of WWII touched down, Jimmy Stewart entertained one last romance—and it almost led to marriage. One of his longest and most high-profile relationships was with screen legend Olivia de Havilland. In fact, de Havilland somehow even managed to get the confirmed bachelor to propose to her—but it had a bitter end.
32. He Wasn’t Ready For Commitment
After Stewart popped the question, De Havilland rejected him. She believed that he wasn’t quite ready for commitment…but she had another reason too. You see, while courting Stewart, De Havilland had had her head turned by the director John Huston. Totally in love with another man, she left Stewart high and dry. Of course, as we’ll see later, Stewart’s journey towards the altar would become even more fraught.
33. He Wasn’t Heavy Enough
Jimmy Stewart came from a passionate and patriotic family, and so when WWII descended, he didn’t hesitate to get involved. In fact, of all the major American movie stars, he was the very first to sign up. He encountered a slight problem, however. Because of his notoriously gangly frame, he was too light to be accepted into the army.
It took a few months for him to bulk up, but by February 1941, he was well on his way to defending his country. And as we’ll see, his traumatic experiences returned him to Hollywood a completely changed man.
34. He Wanted Some Action
While many celebrities enlisting in WWII got confined to symbolic roles, Stewart refused to sit on the sidelines. Following his passion for aviation, Stewart became a pilot and begged to be put in the fray. Astonishingly, he rose from the rank of private to colonel in four years, fought in Germany, and earned the prestigious Croix de Guerre.
However, during his service, Stewart still managed to find someone to keep him warm. At a club intended for servicemen, the Hollywood Canteen, he met his next conquest, Dinah Shore.
35. He Betrayed Her
Maybe all of Stewart’s hesitant ex-girlfriends knew what they were doing. In 1942, Stewart committed the ultimate betrayal. He had been dating actress Dinah Shore and was finally ready to tie the knot. That is, until he wasn’t. Before they got to the Las Vegas chapel, Stewart got cold feet and called the whole thing off.
Compared to the horrors of WWII, however, a disappointing romance was the last thing on his mind.
36. He Kept His Lips Sealed
Stewart staunchly refused to talk about his time in battle, but we do have chilling clues about his experiences. According to one of his biographers, the conflict affected him almost literally down to the bone. He was never a big eater, but he spent long periods during the war eating almost nothing, or else surviving off peanut butter and ice cream. But the horrors didn’t end there.
37. He Lost Them All
Stewart flew on 20 missions, and as time wore on, his distress only mounted. He couldn’t sleep or eat—and the worst was still yet to come. One day, Stewart’s squadron went on a raid without him, and his worst nightmare came true: It turned into a brutal massacre. A single mission wiped out 130 of his men in one fell swoop. The loss of so many of his companions devastated him.
When the fighting ended and he returned to Hollywood, Stewart brought all his rage and pain with him.
38. He Was Unrecognizable
When Stewart reunited with his family after his service, his appearance shocked them to the core. He looked aged and emaciated, and even more startling, he had a commanding edge to him that hadn’t been there before. To make matters worse, his acting prospects were scarce. He even considered quitting acting for good and returning to work for the family business.
However, fate had another plan in store for him—and it would lead him to his most famous film yet.
39. He Had A Second Chance
Jimmy Stewart credits Frank Capra with sparking his next chapter. It’s a Wonderful Life is now a bonafide Christmas classic, and when Capra was casting for the lead George Bailey, both Stewart and his BFF Henry Fonda were up for the part. In the end, though, Capra knew Bailey’s nearly-unerring optimism and goodness were difficult to play and, as he said, “I knew one man who could play it…James Stewart.”
But at first, the part didn’t enthuse him at all.
40. He Didn’t Want The Part
Following his return to Hollywood, Stewart was asked what kind of film he wanted to act in—and his reply was downright heartbreaking: “A comedy, I have to make a comedy. The world has seen too much trauma and horror and suffering.” So when Capra approached him with It’s a Wonderful Life, it was not the kind of role he had in mind.
When he learned that his character eventually considers suicide, he was scandalized. Of course, with very few options left to him, the actor had no choice but to begrudgingly take the role on.
41. He Worked On A Nightmare Set
Though we now see It’s a Wonderful Life as a feel-good, even schlocky Christmas movie, few people know just how nightmarish it was behind the scenes. Stewart, newly returned from war, was reportedly tense the entire time. His co-star Donna Reed even once admitted, “This is not a happy set.” And Stewart’s downtrodden behavior didn’t end there.
42. He Changed His Mind
Throughout filming, Jimmy Stewart constantly questioned his own abilities and wondered whether he should just throw in the towel. However, a conversation with his co-star Lionel Barrymore changed everything. Reportedly, Barrymore asked him, “So, are you saying it’s more worthwhile to drop bombs on people than to entertain them?” This shook Stewart to the core.
He suddenly realized that acting was still a worthy pursuit. In fact, his role in It’s a Wonderful Life offered the damaged actor opportune moments of catharsis.
43. He Gave It His All
Jimmy Stewart took all of his rage and hurt and channeled it into some of the most heartwrenching scenes from the Capra classic. Unfortunately, all the effort and personal strife he injected into his performance couldn’t make the film a success. Although it might sound shocking now, It’s a Wonderful Life was not a huge hit upon release. In fact, it didn’t even make enough to cover its production costs.
Frustrated with the film’s failure, Stewart turned his ire on one person in particular.
44. He Blamed Her
According to Donna Reed’s daughter, Mary Anne Owen, Jimmy Stewart blamed her mother for the film’s unpopularity. Incredibly disturbed by its sad performance at the box office, he needed someone to pin it on—and that just happened to be Donna Reed. According to Owen, “…Jimmy Stewart couldn’t understand why the movie didn’t do well, but that’s why they never did another movie together. He blamed her, because she wasn’t as well known.”
Little did he know, the film would one day have an unprecedented revival. Today, It’s a Wonderful Life is considered one of the best films ever made. At the end of the day, even Stewart ended up changing his tune: Of all his films, it was his favorite one.
45. He Became The Scapegoat
Unfortunately for Stewart, many of his most acclaimed films didn’t receive recognition until much later. He famously worked with Alfred Hitchcock in thriller classics like Rear Window and Vertigo—until the director dealt him a cold-hearted betrayal. Vertigo was initially a critical and commercial failure, and Hitchcock blamed it on the fact that Stewart looked too old, which, you know, sometimes happens when you spend four years in brutal combat. And that wasn’t all.
46. He Was Too Old-Looking
Sadly, Hitchcock had one more betrayal hidden up his sleeve. When it came time to cast his next film North by Northwest, Hitchcock passed the very eager Stewart over. Instead, he cast the more youthful-looking Cary Grant—who was actually four years older than Stewart. Ouch. But while Stewart grappled with these career disappointments, his romantic life became as stable as it had ever been.
47. He Waved Goodbye To His Playboy Days
As we already know, when it came to romance, Jimmy Stewart was rather a man about town. However, once he hit his forties, this “Great American Bachelor” finally found the one woman he could settle down with for life: Gloria Hatrick McLean. However, their romance started off on the wrong foot—and the story of how they met was utterly embarrassing.
48. He Made A Horrible First Impression
Stewart first met his future wife at a Christmas party in 1947, only this was a party that he crashed. Not only that, but he also became completely intoxicated over the course of the festivities. His wild behavior left Gloria Hatrick with a sour taste in her mouth. Luckily for Stewart, however, he’d have a second chance to make amends.
The next year, Stewart’s good friend Gary Cooper invited him to a dinner party. Hatrick just so happened to be there, and during their second meeting, the abashed actor was able to charm his way back into her good graces. The rest was history.
49. He Was A Devoted Husband
By all accounts, Stewart’s marriage to Hatrick in 1949 put an end to his playboy adventures. From then on, he remained completely devoted to Hatrick and never cheated on her. His children also praised him for being a wonderful father. Although his daughter later admitted that “he wasn’t a hands-on dad,” Stewart led by honest example. Still, parenthood wasn’t always easy for Stewart…
50. He Lost A Son
Stewart’s marriage to Hatrick gave him two adopted sons, and then in 1951, the happy couple welcomed twin daughters. Unfortunately, his parenting experience brought him face to face with unspeakable tragedy. After his own hard work in WWII, Stewart expected his sons to enroll in the Army—but this patriotism came at a heartbreakingly high cost.
In 1969, his eldest son Ronald tragically died while deployed in Vietnam. However, this wasn’t Stewart’s first encounter with grief. Only nine years earlier, he’d faced one of the most devastating losses of all.
51. His Old Flame Met A Tragic End
Although Jimmy Stewart adored his wife, he still felt deeply for his old love, Margaret Sullavan. Sadly, she was doomed to a heartbreaking end. While Stewart managed to hold on to his career despite his age, Sullavan wasn’t so lucky. She began to lose her hearing and eventually suffered a full mental breakdown. Her life came apart at the seams, and she died by accidental overdose in 1960…Stewart’s reaction to her passing was unbelievable.
52. Her Loss Broke Him
Stewart’s wife later confessed that Sullavan’s death completely broke him: “He became something of a recluse for a while…He lost the spark that had always been there…the spark went out not with the failure of his films but with the death of Margaret Sullavan.” Unfortunately, Stewart would also outlive Gloria herself, and he never truly recovered from her passing.
53. His Last Words Were Heartbreaking
After Stewart’s wife Gloria passed on in 1994, the heartbroken actor was reportedly “lost at sea.” When he left this Earth just three years after her, his tear-jerking last words were allegedly, “I’m going to be with Gloria now.” On July 2, 1997, 89-year-old Jimmy Stewart died of heart failure. But it was far from a lonely end.
He was surrounded by his family and friends, and all of America mourned his passing. As President Bill Clinton commented upon the news, the country had lost a “national treasure…a great actor, a gentleman, and a patriot.” We couldn’t agree more.
54. His Boss Thought He Was Gay
Except for a couple of bumps in the road, Jimmy Stewart’s reputation has remained unsullied and wholesome. However, Stewart’s early years hid at least one dark secret. You see, under MGM’s Louis B. Mayer, Stewart came up against some prejudiced criticism. Mayer looked at 25-year-old Stewart’s romantic inexperience and worried that audiences might start to think that Stewart was gay.
To remedy this, he came up with an abhorrent solution.
55. He Was A Victim Of Manipulation
To no one’s surprise, Mayer just happened to own a private brothel where his players often went to take the edge off—and it boasted a twisted assortment of after-work shenanigans. MGM scout Bill Grady allegedly told Stewart, “Jim, if you don’t go and give a manly account of yourself at least a few times, Mayer and the others will think you’re gay.” He pointed poor Stewart in the direction of the brothel, and the reluctant star fell prey to this horrible manipulation.
In the end, such extremes only illustrated the corrupt evil behind Hollywood’s studios. Luckily, Stewart pushed through Mayer’s derision and proved himself to be one of Hollywood’s most eligible bachelors. With his long list of romances, a couple of great love stories, and an extraordinary career, his legacy will forever be golden.