‘Teen Wolf’: 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.
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7. Stiles talks about dogs with Lydia ("Chaos Rising")
Stiles over-exaggerates things in a dramatic way that has always been hilarious to viewers, and this moment is no exception. In Season 3 Episode 2, Scott’s pack dealt with people being sacrificed and had to identify the culprit. Stiles, who is preoccupied with Lydia (Holland Roden) being a potential target because she owns a dog, began a long yet hilarious discussion about the threat at hand, trying to convince her to get rid of her dog for her own safety. Stiles’ deep concern for Lydia’s wellbeing was always endearing.
6. Stiles tries to fix his Jeep ("The Dark Moon")
Stiles’ favorite thing in the entire world (after Lydia, Scott, and his dad) was his Jeep. He took his car on every single adventure with the supernatural pack, so it was amusing when it broke down after being involved in too many dangerous situations. One of these scenarios occurred when Stiles traveled down to Mexico to find one of their friends, Derek Hale (Tyler Hoechlin), in Season 4 Episode 1. The car broke down in the middle of the desert, and the group was stranded with no food or water. Stiles didn’t know how to fix his car but tried nonetheless with Lydia’s help, beginning a funny discussion about his (nonexistent) mechanical skills. Needless to say, we wouldn’t trust Stiles in other situations like this.
5. Stiles gets punched by Derek ("Chaos Rising")
Stiles and Derek are one of the most beloved duos of the series because of their snarky and sarcastic banter, but they’re also ready to save each other at a moment’s notice. One of this pair’s most hilarious moments is in Season 3 Episode 2, in which the duo, alongside Scott, tried to get into the city’s bank vault where the Alpha werewolves were situated. After hearing a few mechanical engineering facts from Stiles (we love nerdy men), Derek pointed out that he could break a stone wall with his fist, and the two began bickering about Derek’s strength. Derek punched Stiles’ hand to prove him wrong, and Stiles walked away whimpering.
4. The chains fall off Stiles' locker ("Omega")
Stiles and Scott have been best friends since childhood. Everything changed when Scott became a werewolf, but some things with these two never change. One of their best moments is in Season 2 Episode 1, when Scott reassured Stiles that he learned how to control himself during the full moon transformation (he couldn’t do that in Season 1 and attacked Stiles by mistake). To be more secure, Stiles used a different approach to keep Scott away from harming anyone again: chains. It was a good idea in theory, but he didn’t secure them well enough. The chains fall off the locker and everyone at school saw, including Coach Finstock (Orny Adams). Coach mercifully walked away and pretended nothing happened, and Stiles welcomed the assist.
3. The Batman and Robin reference ("Pack Mentality")
In Season 1 Episode 3, Scott had a nightmare that he killed a school bus driver. But it wasn’t a nightmare — the accident really happened, making Scott fear that it was him who did the killing since he was still learning how to control his powers. He set off to investigate the crime scene himself and told Stiles to play lookout. Offended by the direction, Stiles began a hilarious argument in his defense, drawing a comparison of the two to the famous DC Comics duo, Batman and Robin. It’s an iconic scene from the show’s early years that highlights Stiles and Scott’s endearing dynamic.
2. Stiles fainting over the sight of blood ("Tattoo")
After surviving the dangerous events that unfolded in the second season, the third season began with Scott going to get his first-ever tattoo alongside his best friend. In Season 3 Episode 1, Stiles confessed he felt squeamish at the sight of blood and fainted while watching Scott getting inked. You’d think that fighting supernatural creatures with Scott’s pack for two seasons straight would put an end to this fear, but no! To frequently face deadly odds and still be affected by the little things showed that even the scariest of circumstances couldn’t change this quirky character, and we love him for it.
1. Stiles vs. the vending machine ("Omega")
Fans have always loved the small detail that whenever Stiles is trying to concentrate or just needs a break from all the supernatural chaos, he reaches for a snack. This is first seen in Season 2 Episode 1, when he’s at the hospital looking over Lydia like the lovesick puppy he is (she was hospitalized after being attacked in the Season 1 finale). Stiles headed to the vending machine for a much-needed snack break, but the food got stuck on its way out. Not to be denied a treat, Stiles tried moving vending machine by pulling and kicking it, resulting in it crashing down and the glass shattering to pieces. It the show’s funniest scene, in our book.
From TV Guide Magazine
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