The Bessie Stringfield Documentary Is An Oscar Contender, and It's About Time

If you're already a motorcycle rider, you don't need me to tell you how good it feels. You already know. 

But if you're not, and you've been thinking about joining our ranks, then if you don't already know about Bessie Stringfield, I and a growing number of people hope you'll become well acquainted. Although the woman herself is no longer in this world, her story has inspired riders for generations.

Black riders, women riders, riders who share both those identities, and riders who don't continue to find inspiration in learning about Stringfield to this day. In that way, I suspect (and hope) she'll live on forever, and surely the fact that To Myself, With Love: The Bessie Stringfield Story continues to rack up film festival awards and nominations can only help. 

It's now the beginning of December, and the makers of the Bessie Stringfield doc just shared that the film is now officially a real, live Oscars contender. The category for which it's in contention is "Best Documentary Short Film." There's no telling what will happen next, but it's definitely an exciting development, both for filmmakers and for all who want Stringfield's story to be shared more widely.

Just who was Stringfield, and why should more people know about her? For those unfamiliar with Bessie Stringfield, she was a pioneering rider who, in many ways, embodied the true spirit of motorcycling. To summarize her story in one sentence: She was a Black woman who rode across the United States multiple times, starting in the 1930s, and who refused to let anyone or anything stand in her way. 

Don't just gloss over that sentence; think about it. Stand in it. Let your mind and your knowledge of historical conditions really steep in the challenges she faced. I had the chance to speak with two of the folks involved in making this film at the beginning of 2024, and I suggest you take a few minutes to read that interview and learn more about both Stringfield and the film.

Jumping forward in time from that interview to now and To Myself, With Love: The Bessie Stringfield Story doesn't currently have additional screening dates listed on the official website at this moment. Throughout 2024, it's been making the rounds of film festivals and has both been nominated for and won several awards. Can it also win an Oscar? We'll have to wait and see, but it'd be pretty amazing if it did.