Did a 20-Year-Old Yearbook Photo Predict This Year’s Oscars?

A 20-year-old yearbook superlative might finally become true during this year’s Best Actress race at the Academy Awards. In a 2004 photo that has since gone viral, Killers of the Flower Moon star Lily Gladstone poses for her senior-year award: “Most Likely to Win an Oscar,” which she won alongside one of her classmates and theater pals, Josh Ryder.

With plenty of Oscar pundits predicting a historic win from Gladstone, who plays Mollie Burkhart in Martin Scorsese’s latest film, this prophecy could come to fruition. Was that year’s Mountlake Terrace High School yearbook magic? And does this mean there’s a win in Ryder’s future, too?

“I don’t foresee that happening,” Ryder says on a Zoom this week with The Daily Beast’s Obsessed. Since the photo was taken, he’s left the acting world; now, he co-owns and works as a chef at a restaurant in Seattle. “As cool as that would be, I’m not the same person that I was 20 years ago.”

But Ryder, who remains friends with Gladstone, is extremely enthusiastic about his pal’s huge potential in this awards season, and has been sharing photos in support of her on Instagram along the way. He watched Gladstone go on to win the Golden Globe for Best Actress in a Drama live on Sunday, still finding time to cheer her on while working a shift at his restaurant.

“It made my day, easily,” Ryder says, adding, “It was pretty fuckin’ cool to see ‘Golden Globe winner Lily Gladstone.’ Damn! That’s something that’s never going to go away. That belongs to her now.”

As the excitement for awards season builds, Ryder chatted about the magic behind that foreshadowing yearbook photo, what Gladstone was like as a younger actor, and how their friendship has evolved over the years.

This interview has been condensed for length and clarity.

Let’s start with the yearbook picture. Can you tell me how that photo came to be?

That picture is from our senior yearbook. We graduated from Mountlake Terrace High School in 2004. There were a bunch of categories—best dressed, smartest. [Ours] was “most likely to win an Oscar.”

And I’m assuming you both won that category from doing theater together.

I first met Lily doing theater in high school. She and I were in a production of “Our Town” by Thornton Wilder. Then, I think we did three productions together over the years. That’s where our friendship grew. When senior year came around, and the superlatives were getting voted on, I had done a lot of productions in high school. That was my tribe. For both of us, our people were weird theater kids. We both still probably gravitate to that community.

How did winning that superlative feel at the time, and how does it feel now that this Oscar win may actually happen?

It was neat! It was certainly a pat on the back for the ego. Never in my wildest dreams did I think that that would come to fruition. It’s very fucking cool that Lily may very well go the distance. It’s so surreal. I’m over the moon for her.

Are you two still in touch?

Yeah! The last time I saw her prior to Killers was 2018. She wrote and produced a short VR film that highlighted Mildred Bailey, an Indigenous jazz singer responsible for springboarding Bing Crosby’s career. She cast me in that—I got to play Bing Crosby in the short. That was the last time I saw her. Then the pandemic happened.

Then she got a little busy.

Understandably! Since [Killers] came out, and the picture of us from high school has [recirculated], we’ve texted more. When we saw [her 2023 movie] Fancy Dance, it was at a theater just a few blocks from my place. I’m a part-owner of a restaurant not too far away, so she got to eat there and then we saw Fancy Dance. She’s one of those friends that I feel very comfortable [picking] things up after a couple months, after a couple years. Her world is changing a lot, and mine is too. I hope to maintain a friendship with her until the end of my days.

Since the photo has gone viral, folks are wondering if the Oscar prophecy will come true for you, too. Are you still acting?

I made a career transition. I was acting semi-professionally until 2015, and then I needed to take a break. My mental health was in a really bad spot. It’s a very tough way to earn a living. Since then, I’ve worked solely in the restaurant industry.

That’s another part of Lily: She’s done the work. She’s stayed in the game. The highs are high, but the lows are low. She’s stayed in it and weathered some probably very severe droughts when things weren’t going her way.

A lot of the discussion about the yearbook picture started off with, “Josh Ryder must be kicking himself—he’s not winning an Oscar!” But you’re just happy to see a friend succeed.

I saw people being like, “You should be posting this everywhere!” But I’m not interested in using this moment for personal gain. This is Lily’s moment. What this moment does not need is a white guy elbowing his way into the table and saying, “Make this about me!” This is about Lily, who has done the work, who has a really unique vantage point as an Indigenous woman, and someone who is extremely talented. This is her time to shine, and my favorite role that I get to play right now is being her cheerleader.

You posted about seeing the movie with some high school theater friends. What was that experience like?

At first, it was kind of like jumping into water. Like, “Ah! That’s Lily up there!” And then, I kind of settled in and got to enjoy her performance. Lily is a master of subtlety and intensity through stillness. Even back in the day, in high school, she was always a really dedicated performer who took it really seriously. That’s her bread and butter, the things that she doesn’t say. The subtlest of gestures.

How do you think Lily’s grown as an actor since you were performing with her in high school?

What has changed the most for her has been being able to tell stories that highlight Indigenous stories. Back in the early 2000s, in high school—but also in mainstream media, too—there wasn’t a lot of that. She just needed Hollywood to catch up, basically. Killers of the Flower Moon is showing that the needle is moving.

That’s her other brilliance: She’s not just going to walk through the door. She’s going to keep the door open and help lift up other Indigenous creators and performers. But also, when those opportunities aren’t given to her, she’s like, “I’m gonna make them myself.” She’s going to swing for the fences. I’ve got a lot of love for Lily, but that’s where the respect comes in.

Do you already have plans to watch the Oscars?

We are in the process of planning an Oscar party, which is hopefully going to be at our high school. Our drama teacher is still there, so she’s doing the leg work to get the space. We’re hoping to get some Indigenous food trucks there. The current student body is going to mix with some alums. I’m really looking forward to getting to share that with this younger generation. We’re gonna blow the roof of that place!

Another thing that’s been great about this is the sense of community that her ascent has brought about. I’ve been chatting with people online that I haven’t chatted with in 15, 20 years. And I hope—this is a very unique example, winning a Golden Globe, that’s probably never going to happen again to our high school group—that it sets a trend where we celebrate victories with each other.

What is your favorite memory of Lily?

I remember one time, after high school and shortly after college, we got dinner. I went to school for theater, and I remember talking to her about how some characters that you play really stick with you, for better or for worse. We had both played characters that had some capital-T trauma. Putting yourself in that space as an actor is not always a free choice. There’s some collateral of your own mental well-being. I remember it being really comforting and cool to talk with a fellow performer about the burden or cost of playing characters that have some shit that they need to process. I wasn’t alone—that experience wasn’t unique to me.

You asked before about how she’s grown. I remember seeing another interview of her recently with her saying that if she plays a character who has trauma, she tries to give them a physical quirk. She always makes them left-handed, and she’s right-handed. That’s a way of protecting herself, giving herself a physical token to cling onto. To know that she’s taken care of herself as she’s taking on these difficult roles is cool.