When you think of a leather jacket, a switchblade, and a "tough as nails" attitude that hides a shattering amount of grief, you're thinking of Dallas Winston. He’s the guy who didn't want to be "gold." He was already hardened by the streets of New York before he ever stepped foot in Tulsa. But if you’ve ever found yourself staring at the screen or a stage and wondering who plays Dally in The Outsiders, the answer depends entirely on which version of this classic story you're diving into.
Most people immediately picture the brooding, sharp-jawed face of a young Matt Dillon. That’s fair. His performance in the 1983 Francis Ford Coppola film basically defined the character for three generations. But there’s a new era of Dally happening right now on Broadway that’s winning Tony Awards and changing how we see the "toughest" Greaser.
The Original Hood: Matt Dillon’s Iconic Performance
In 1983, Francis Ford Coppola basically rounded up every future A-lister in Hollywood and threw them into a house in Oklahoma. Among them was Matt Dillon. At the time, Dillon was already becoming the "go-to" guy for S.E. Hinton adaptations—he had already starred in Tex and would go on to do Rumble Fish.
Dillon didn't just play Dally; he was Dally. To get into character, Coppola actually wanted Dillon to spend a night in a real jail. Dillon reportedly said "no thanks" to that, but he still brought a level of raw, unpredictable energy to the role.
Why Matt Dillon’s Dally Stuck
Honestly, it was the vulnerability. You see it in the scene where he falls off his chair at the drive-in (which was actually a real accident, by the way, and the actors’ laughter was genuine). You see it even more when Johnny dies. When Dillon screams, "Johnny, don't die!" and loses his mind, it isn't just movie acting. It felt like a guy who had finally lost the only thing he actually loved.
- The Look: Messy hair, the squint, and that specific way he held a cigarette.
- The Ending: His death scene under the streetlights remains one of the most tragic moments in 80s cinema.
- Fun Fact: The blood droplets on his chest during that final scene were so stubborn they wouldn't wash off for a week. The rest of the cast, including Tom Cruise and Rob Lowe, didn't let him live it down.
The New Era: Who Plays Dally in The Outsiders Musical?
Fast forward to 2024 and 2025. The Outsiders has been reborn as a massive Broadway hit. If you’re seeing the show today, you aren't seeing Matt Dillon. You’re seeing a version of Dallas Winston that is arguably more soulful and musically powerhouse-driven.
Joshua Boone (The Original Broadway Dally)
Joshua Boone originated the role of Dallas Winston in the Broadway production. He didn't just play a hood; he played a mentor, a big brother, and a tragic hero. His performance earned him a Tony Award nomination for Best Featured Actor in a Musical.
Boone’s Dally is famous for the song "Little Brother," a gut-wrenching number where he tries to guide Ponyboy while acknowledging his own life is a dead end. He brought a "commanding presence" that made the theater go silent. If you’re looking for the actor who set the gold standard for Dally on stage, it’s him.
Alex Joseph Grayson (The Current Dally)
As of early 2025, the leather jacket has been passed to Alex Joseph Grayson. Taking over a Tony-nominated role is no small feat, but Grayson—who previously blew people away in the revival of Parade—has made the character his own.
Grayson plays Dally with a bit more of a "natural" acting style. He’s been praised for his vocal choices, often choosing to deliver lines with a soft, haunting vulnerability rather than just tough-guy shouting. It makes the character feel incredibly "fresh and alive," even for people who have seen the movie a hundred times.
The Understudies and Tour Actors
Broadway shows are a marathon, not a sprint. Because Dally is such a physically and vocally demanding role, several other actors have stepped into those boots:
- Daryl Tofa: Often noted for bringing an incredible sense of vulnerability to the role.
- Aramie Payton: Known for a high-energy, "powerful" interpretation.
- Tyler Jordan Wesley: The actor taking Dally on the road for the North American tour in 2025.
Dally Winston in Other Media
Believe it or not, there was a short-lived Outsiders TV series in 1990. In that version, the role of Dallas Winston was played by Billy Bob Thornton. Yeah, that Billy Bob Thornton. It was a very different vibe—a bit older, a bit more weathered.
And if you go back to the world of regional theater, you'll find the Christopher Sergel stage play that schools have been performing for decades. In those productions, Dally has been played by thousands of young actors, but the script remains rooted in that same tragic, "nothing gold can stay" energy.
Why the Actor Playing Dally Matters So Much
Dally is the "dark" mirror to Ponyboy. While Ponyboy sees the sunset, Dally only sees the pavement.
Whoever plays him has to balance being a total jerk with being the guy you’d trust with your life. Matt Dillon gave us the "rebel without a cause" cool. Joshua Boone and Alex Joseph Grayson gave us the "soul-searching" tragedy.
It’s a role that demands a lot. You have to be able to handle a rumble, look cool with a switchblade, and then break the audience's heart into a million pieces in the final ten minutes.
What to Watch (or See) Next
If you want the full Dally experience, you've basically got two paths:
- Watch the "Complete Novel" version of the 1983 film. It has restored scenes that give Matt Dillon’s character way more depth than the original theatrical cut.
- Get a ticket to the Bernard B. Jacobs Theatre in NYC. Seeing Alex Joseph Grayson perform "Little Brother" live is something that a movie screen just can't replicate.
Whether it’s Dillon’s 80s grit or Grayson’s Broadway soul, Dallas Winston remains the most complex character in S.E. Hinton's world. He’s the Greaser who tried to be hard so he wouldn't get hurt, only to find out that caring about people is the one thing you can't "tough" your way out of.
To truly understand the character's impact, your next step should be comparing the two most distinct versions. Check out the 1983 film's "Complete Novel" edit to see Matt Dillon's full range, and then listen to the Broadway cast recording of "Little Brother" to hear how the role has evolved into a modern theatrical masterpiece.