My Unforgettable Encounter with Jimmy Stewart

December 27, 2021

Hopefully, everyone is enjoying a relaxing week with friends and family. I’m taking a break this week from writing about cars, so feel free to skip it if you like. However, you’ll miss a heartwarming tale about the time I met the legendary actor Jimmy Stewart. Happy Holidays!


On Christmas morning I woke up early and was enjoying a peaceful morning. I saw that one of the cable channels was playing “It’s a Wonderful Life” all day long. With a cup of hot coffee in hand, I settled in and watched it all the way through. There’s something about George Bailey’s self-sacrifice and his belief that people must look out for each other that seemed even more pertinent this year than most.

As great as that character is, the actor that portrayed him was even better. Jimmy Stewart is someone I’ve admired much of my life, and I was fortunate enough to have once met this accomplished man. It is said that you shouldn’t meet your heroes, but that was definitely not the case with Mr. Stewart. Encountering him was even better, and it left an indelible mark on me. 

When I was in my junior year at the University of Pittsburgh, I read in the newspaper that Jimmy Stewart, who was 80 at that time, was in town to receive a lifetime achievement award. As fans of his movies, my roommate and I thought it might be a final opportunity to see one of the greatest actors of the 20th century. We decided to go try and get a glimpse of him from afar. 

A Hidden War Hero

Most people only knew him through his roles, but he was even more impressive for what he did behind the scenes. Despite already being a major film star, Mr. Stewart was the first major celebrity to enlist in the military at the outset of WWII. Since he was 33 at the time of his enlistment, the Army used his Oscar-winning celebrity status to promote enlistment and war bonds, but Mr. Stewart wanted to fly in meaningful combat duty. 

Col. James Stewart

As a licensed commercial pilot, he was persistent and pleaded with his commander to assign him to train pilots at an airbase in New Mexico on B-17s and B-24s. After a year as a trainer, he got his wish and was transferred to England in 1943, where he was to fly raids over Germany as a B-24 Liberator pilot. 

He flew more than 20 dangerous combat missions as part of the 445th Bombardment Group, including several as the squadron leader, and narrowly missed being shot down by the anti-aircraft fire and fighter planes. As squadron commander, he was known to always join the most dangerous missions which inspired his crew and lifted the morale of the squadron. 

What’s more, is that he didn’t want his celebrity status to be a distraction in combat, so Mr. Stewart flew many of his missions “off the books” (i.e., not on the flight manifest) because, in the event of his death, he didn’t want to steal the attention away from his fellow crew members. 

Croix de Guerre award

By the end of WWII, he was one of only a handful of American servicemen to enter as a private and achieve the rank of colonel in just four years. Mr. Stewart was awarded the Distinguished Flying Cross and other medals, yet he eschewed publicity while in theater and thus his service record is little known. 

Following the war, he stayed active in the reserves and served in the Strategic Air Command, and was certified on the B-47 and B-52. In 1957, Col. Stewart was promoted to the rank of Brigadier General and is the only actor to have ever achieved that rank. He served quietly until he hit the mandatory retirement age of 60 in 1968.

Awkwardly Out of Place 

So for a young guy, I found him to be an impressive man both on and off the screen. If I could see him, I thought that would be pretty cool. My roommate Douglas and I put on our winter coats and took the bus to the hotel where the ceremony was taking place. We didn't have a clue what to expect, especially not a black-tie affair with fancy appetizers and champagne bars. Two college kids in jeans and winter coats were a tad out of place.

We sheepishly stood on the periphery and watched the goings-on. After a half-hour or so, a chime rang and the attendees retreated into the big hotel ballroom. The cocktail area emptied until it was a bunch of waitstaff cleaning up, and us. 

Dejected, we turned to head back to campus. We walked over to the bank of elevators and hit the "Down" button to get to the lobby. After a moment, the bell rang for our elevator. As the doors opened, we saw that the sole passenger was Jimmy Stewart, resplendent in a tuxedo draping over his slender, bony frame. 

He looked exactly like this!

Not one to be shy, we let him step off and I said, "Mr. Stewart, we're so glad to see you. We came down to say 'hi.'” In his wavering voice, he said, "Well, I'm sure glad you did. It's great to see you, fellas!" And he seemed to actually mean it. Even more surprising, he got between us and put his arms around our shoulders and hugged us, and walked with his arms around us for a few steps.

We had picked up the evening's program that was being handed out for the gala, so we asked if he wouldn't mind signing one for each of us, which he did without hesitation. Once he finished, he said that he was “terribly late” and bee-lined for the side entrance to the ballroom. Just like that, it was over. It had all happened so quickly that it took until we had gotten out of the hotel for it to start sinking in.

Years later, after moving around for college, I had lost track of that little slip of paper. One Christmas, I opened a gift and my incredibly thoughtful mother took Mr. Stewart’s autograph and had it framed, along with a pencil sketch of him during his younger years. It is certainly one of my most prized possessions.

I think back to that encounter, and it serves as a frequent inspiration for me. Jimmy Stewart led by example, had a deep commitment to serving others, and never let his values waver, despite his success and fame. Most of all, he was humble and generous enough to share a moment with a couple of out-of-place college kids to show them what a life well-lived looks like.

The autograph from that serendipitous encounter in 1988.

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