Dylan O’Brien’s Most Charming Stiles Moments, Ranked

Dylan O’Brien has had a huge fanbase ever since his breakout role in MTV‘s Teen Wolf (2011-2017). The character he portrayed in the series was a sarcastic yet courageous human, Stiles Stilinski, the longtime best friend of the series’ main lead, Scott McCall (Tyler Posey).

Teen Wolf focuses on the story of Scott, an average teenager living in the fictional town of Beacon Hills, who becomes a werewolf after being bitten while searching for a body alongside his best friend Stiles. This unfolds a series of events that will change his, and his friends’ lives forever.

Teen Wolf stands out from other supernatural teen dramas because it’s a rare show that focuses on werewolves instead of the more common vampires and witches. But it’s the journey of Scott and his friends that really hooks you, and O’Brien’s performance as Stiles did a lot of legwork on that front.

In the years since Teen Wolf ended, O’Brien has broken out into film roles, most recently playing Dan Aykroyd in the Saturday Night Live biopic, Saturday Night. He’ll next star in Twinless alongside writer, director, and costar James Sweeney, and his performance received rave reviews at the 2025 Sundance Film Festival (it’s being hailed as O’Brien’s “career-best performance“).

As O’Brien’s star continues to rise, let’s look back on the role that started it all. Here, we rank O’Brien’s seven most charming Stiles moments in Teen Wolf.

Teen Wolf, Available Now, Hulu