Sister Celluloid

Where old movies go to live

TINTYPE TUESDAY: When Olivia Met (and Almost Married) Jimmy

You know who almost got married? Olivia de Havilland and Jimmy Stewart.

Can you imagine?

But when they got to the marriage license bureau, they were intercepted by the Minister of Fabulousness, who told them it would be just too much for them to join together in wedlock.

Okay that’s not actually what happened. Here’s what did.

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In December 1939, Olivia and Jimmy were both bound for New York—she to attend the city’s premiere of Gone With The Wind at the Astor Theatre, and he to visit his sister for Christmas. Irene Mayer Selznick—daughter of Louis B., wife of David O., and no slouch herself in the mover-and-shaker department—suggested to Jimmy’s agent, the legendary Leland Hayward, that his client escort Olivia to her big event. And Jimmy, who was intrigued when he’d met the actress briefly in Hollywood, seized on the chance to get to know her better.

“Jimmy met me at LaGuardia airport,” Olivia recalled to James Fishgall, author of Pieces of Time: The Life of James Stewart. “He even had the limousine drive out to the airfield. We were both quite shy and ventured one word at a time in our conversation.” Those must’ve been some words: the two were quickly inseparable, dining together almost every night and ducking into the latest Broadway shows, including Paul Osborn’s Mornings at Seven, directed by Jimmy’s Princeton pal Josh Logan.

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The new couple were closer than ever when they headed back to Los Angeles—where actual hijinks ensued, followed closely by shenanigans. One night, Jimmy pulled up to Olivia’s Spanish colonial home in his new LaSalle convertible. As he showed off the car in the driveway, it suddenly began to creak and groan to life. They soon discovered that the Hollywood Hills are just about the worst place to be when your brakes come unglued. As the glamorous pair—decked out in their evening best—frantically scrambled after the runaway coupe, it gained speed, bumping into parked cars and bashing finely manicured shrubs to bits, finally slamming into a telephone pole at the bottom of the steep incline. Jimmy was mortified, but Olivia thanked him for the laugh as they trudged back up the hill and bundled into her car to resume their date.

Another evening, Olivia and dinner guest Maureen O’Hara pretended to become violently ill after eating a fish Jimmy had caught. “But he didn’t pay the slightest bit of attention,” O’Hara remembered. “He knew!”


Already a licensed pilot, Jimmy loved to take Olivia out over the Pacific, and even gave her a few flying lessons. They also tooled around with his model airplanes, picnicked in the woods (with a Victrola in tow!), and sometimes just bundled on the sofa, each with a book, eventually dozing off. So close were they that by the spring of 1940, rumors of an impending elopement were popping up in fan magazines.

But Jimmy and Olivia, whose worldview stretched far beyond the petty contrivances of Hollywood, had more urgent issues on their minds. The Nazi threat was growing monstrously, and England—where Olivia’s parents were born and her father still lived—was largely standing alone against the Third Reich as other European countries began topple. In August 1940, when shooting wrapped on The Philadelphia Story, Stewart helped organize a benefit for the beleaguered British forces. Held at the Sam Houston Coliseum in Texas, the show featured Olivia, Tyrone Power, Mischa Auer and Jimmy’s close friend and one-time roommate Henry Fonda, who played the cornet to Jimmy’s accordion and teamed up with him on a magic act.

dehavilland-stewart-6James Stewart, Olivia De Havilland 1938 Copyright John Swope Trust / MPTV

In March 1941, Jimmy enlisted in the Army, a full nine months before the bombing of Pearl Harbor. He and Olivia tried to remain close, but it was not to be. The following year, Olivia began seeing John Huston, her director on In This Our Life (Huston and Errol Flynn once reportedly came to blows over her), and her relationship with Jimmy officially ended.

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At some point during their year and a half together, Jimmy, who had already squired half of Hollywood, did propose—but the ever-wise Olivia, though eight years younger, was skeptical about his level of maturity. “I think his offer of marriage was just a frivolous thing on his part,” she said years later. “Jimmy wasn’t ready for a wife—I guess he still had a few more wild oats to sow.”

“I think they got closer to the altar than was known at the time,” Jimmy’s friend, former MGM publicist Jerry Asher, recalled in Lawrence Quirk’s James Stewart: Behind the Scenes of a Wonderful Life. “But they ‘scaredy-catted’ out of it. They were a lot alike, Livvy and Jim. Prim, well brought up, decent, considerate, but as romantic and sexy as any guy or gal around.”

Whatever regrets the two may have had about their parting, we’ll never know. But both later said they wished they’d made a film together. Toward the end of their careers, they did appear, though separately, in Airport ’77 and the 1986 miniseries North and South, Book II.

And in 1950, it was Jimmy who presented Olivia with her Best Actress Oscar for The Heiress.


Ironically, Paul Douglas introduces Jimmy by quipping about how his recent marriage ended his long reign as Hollywood’s most popular bachelor. Then Jimmy, who seems delighted as he announces Olivia’s name, bows ever so slightly and politely shakes her hand. Ah, to know what he was thinking, or maybe remembering.

A post-script of thanks to you, readers and bloggers: Recently, my Sister Celluloid and Twitter mailboxes have been lighting up like the switchboard in an old movie when news is breaking—Mr. and Mrs. High Society are getting divorced, the stock market is crashing, that sort of thing. Lots of readers and bloggers have written to tell me that just a coupla weeks after I started Tintype Tuesdays in early September, a blogger out there began doing exactly the same thing—doing a photo feature every week on a particular day, with all the pix revolving around a certain theme, and even using an alliterative title tied to the day of the week! Well, hey, to quote one of my favorite films, The More the Merrier. Still, it was awfully kind of so many people to feel compelled to call this to my attention. I’ve said it before, but it bears repeating: The best thing about starting Sister Celluloid is all the people I’ve been lucky enough to meet, virtually and otherwise. I really do wish we could all find a nice pub somewhere to spend actual time together. Barring that, you have my love and gratitude right here!

TINTYPE TUESDAY is a weekly feature on Sister Celluloid, with fabulous classic movie pix (and usually backstory!) to help you make it to Hump Day! For previous editions, just click here—and why not bookmark the page, to make sure you never miss a week?


  1. I had NO idea about any of this.

    I also wish they’d made a film together…

    • I didn’t know either until recently! How was this under our radar?!? 🙂 And yes, imagine them in a movie together!! The height difference alone is adorable…

  2. I didnot know this info-thanks for letting me in on this news from classic Hollywood-neat to read about this romance.

  3. Fascinating! I have always had such a crush on Jimmy Stewart. One of the greats. They don’t make them (in Hollywood) like that anymore! 🙂

  4. Beautiful pictures! Great piece!

  5. I never knew any of this and I thank you for writing this piece. Fascinating! I love old Hollywood!

    • Thank you so much for your kind words, Cathy! I loved writing this!! ❤

  6. I had no idea this happened, but they would have been so adorable together — on screen or off. She may have been wise to turn him down though. (Didn’t he eventually marry and stay married for decades?) Fun post and glorious pictures! 🙂

    I’m looking for participants for the 2020 Olivia de Havilland Blogathon, taking place over her birthday on July 1 & 2nd. Short notice, I know, but I was waiting for someone else to host it. LOL I would love to have you contribute, if you’d be interested — you can find the details and sign-up at

    Thanks for considering it! 🙂

    • I would love to but am swamped with real-life work right now, catching up after lockdown! I will be sure to check it out though!! ❤

  7. Laila

    This is so fantastic! Thank you for sharing! This might be a dumb question but I was just wondering if that is Jimmy or John Huston in the pool pictures with Olivia? Thanks! 🙂

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