When you think about the late Anton Yelchin, your mind probably goes straight to Star Trek or maybe that gut-wrenching performance in Like Crazy. He had this way of looking at his co-stars like they were the only person in the room. But there’s a specific, recurring creative spark he shared with Olivia Thirlby that feels like a time capsule of indie New York cinema. They weren't just two actors who happened to be in the same movie once; they were a duo that captured a very specific kind of awkward, youthful sincerity across multiple projects.
Honestly, it’s rare to see that kind of natural rapport. You’ve seen it before—two actors who just get each other’s rhythm. For Thirlby and Yelchin, that rhythm was built on the streets of Manhattan, usually involving a fair amount of cigarettes and high-concept romantic drama.
The Central Park Spark: New York, I Love You
The first time most of us saw them together was in the 2008 anthology film New York, I Love You. Specifically, they starred in the segment directed by Brett Ratner. It’s a bit of a weird one, looking back. Anton plays a kid who gets dumped right before his prom. In a weird turn of events involving a pharmacist played by James Caan, he ends up taking the pharmacist's daughter—played by Olivia—to the dance.
The twist? Her character is in a wheelchair.
It’s a short, six-minute story, but the chemistry is what saves it from being just another "lesson of the week" bit. There’s this scene in Central Park where they’re just talking, and you can see the genuine curiosity in Anton’s eyes. Thirlby, meanwhile, plays the role with a sharpness that keeps the sentimentality from getting too sugary. They nailed that specific brand of "first date jitters" that feels totally authentic even in a movie that's basically a series of vignettes.
👉 See also: Why Taylor Swift People Mag Covers Actually Define Her Career Eras
Why Olivia Thirlby and Anton Yelchin Worked So Well in 5 to 7
A few years later, they reunited for 5 to 7, a 2014 romance that’s become a bit of a cult favorite for people who love movies about writers and complicated relationships. Yelchin plays Brian, a struggling writer who falls for a married French woman. Olivia Thirlby plays Jane, who is—wait for it—the mistress of the French woman’s husband.
It sounds like a messy soap opera, but the movie treats it with this soft, European-style nonchalance.
What’s interesting is that while they aren't the primary romantic interest for each other in this film, their scenes are the backbone of the movie’s "literary" feel. Jane is a book editor. Brian is an aspiring novelist. When they talk, it feels like two people who actually live in the world of words. Thirlby brings a grounded, slightly older-sister energy to the role, coaching Yelchin’s character through the bizarre rules of his affair.
- The Dialogue: It's fast, witty, and deeply New York.
- The Dynamic: They share a professional and personal bond that feels more stable than the central affair.
- The Vibe: It’s basically a love letter to the Upper East Side.
Basically, their connection in 5 to 7 was the bridge between the "American innocence" of Yelchin’s character and the "European sophistication" of the world he was trying to enter. Without Thirlby’s character to ground him, Brian would have just seemed like a lost kid. She made his transition into adulthood feel real.
✨ Don't miss: Does Emmanuel Macron Have Children? The Real Story of the French President’s Family Life
A Friendship Beyond the Screen
While they weren't a couple in real life—Olivia has been married to Jacques Pienaar since 2014—there was clearly a deep mutual respect. Actors who work together multiple times usually do so because directors see a "shorthand" between them. When Anton passed away in that freak accident in 2016, the loss was felt across the entire indie film community. Thirlby, like many of his former costars, has spoken about his incredible talent and the kind of light he brought to a set.
He was the kind of actor who didn't just show up; he lived in the character. Thirlby is similar. She has this "in control" presence that directors love. Seeing them together was like watching two people speak a secret language.
What Most People Get Wrong About Their Collaboration
Some fans assume they were a "thing" because their chemistry was so effortless. In reality, it was just great acting and a shared history. They represented a specific era of the "Manhattan Indie"—those movies shot in the fall, featuring lots of scarves, benches, and existential conversations about art.
If you go back and watch their scenes in New York, I Love You and 5 to 7 back-to-back, you see the growth. They went from playing teenagers at a prom to adults navigating the ethics of open marriages and the publishing industry. It’s a micro-evolution of two of the best actors of their generation.
🔗 Read more: Judge Dana and Keith Cutler: What Most People Get Wrong About TV’s Favorite Legal Couple
Where to Revisit Their Work
If you’re looking to dive back into this specific corner of cinema, start with 5 to 7. It’s available on most streaming platforms like AMC+ or for rent on Amazon. It’s a quiet movie. Don’t expect explosions or high-stakes chases. It’s a movie about people talking in beautiful rooms.
Then, find the Ratner segment of New York, I Love You. It’s definitely of its time, but seeing a young Anton Yelchin and Olivia Thirlby navigate a prom night is a bittersweet reminder of the talent we lost and the talent we still have.
Actionable Next Steps
If you want to explore more of their individual work that captures that same "indie soul," here is what you should check out:
- For Anton Yelchin: Watch Like Crazy. It’s the definitive "long-distance relationship" movie and features his best work.
- For Olivia Thirlby: Check out Juno (of course) or her more recent work in Oppenheimer to see how she’s transitioned into massive ensemble pieces.
- The Double Feature: Watch 5 to 7 followed by Before Sunrise. They share a similar DNA of "conversation as romance."
The legacy of Olivia Thirlby and Anton Yelchin isn't just about the movies they made, but the way they made them feel—intimate, a little bit messy, and entirely human. Regardless of whether you’re a die-hard fan or just looking for a good weekend watch, their collaborations are a masterclass in on-screen chemistry.