Dylan O’Brien: Ranking His Best Career Performances

American actor Dylan O’Brien has had several standout performances in his career. Like many other actors before him, O’Brien began his career as a teen actor. Born in New York City on August 26, 1991, Dylan O’Brien made his debut in 2011 at age 19.

Since then, O’Brien has been featured in lead and supporting roles in several big-budget movies. Although he’s been cast fewer roles in the last few years, O’Brien has stayed busy with several upcoming films. With a career spanning 13 years, these have been Dylan O’Brien’s best performances.

7. Not Okay

Dylan O'Brien in Not Okay

In Quinn Shephard’s 2022 satirical black comedy-drama Not Okay, Dylan O’Brien played a supporting role as Colin. His character is introduced as a famous social media influencer with a carefree, party-loving lifestyle. Colin was known for his superficial charm, wild personality, and obsession with his online image. The character was a love interest for the movie’s protagonist, Danni Sanders (Zoey Deutch). Danni became infatuated with Colin while trying to gain popularity through social media. In Not Okay, Dylan O’Brien’s character represents the shallow and self-confessed side of internet culture that the movie critiques.

6. The Outfit

Dylan O'Brien in The Outfit

Although his character is killed off in the movie, in the 2022 The Outfit, Dylan O’Brien played Richie, the son of a Chicago Irish mob boss, Roy Boyle (Simon Russell Beale). The movie is set in the mid-1950s and revolves around a tailor, Leonard Burling (Mark Rylance). Leonard runs a shop that is a front for laundering money for the local crime family. Despite being the son of the Irish mob boss, he’s shot and killed by the mob’s chief enforcer, Francis (Johnny Flynn).

5. Teen Wolf

Dylan O'Brien in Teen Wolf

MTV’s supernatural teen drama series Teen Wolf was Dylan O’Brien’s television debut. Over a decade later, it is still his biggest project on the small screen. In Teen Wolf, O’Brien plays Stiles Stilinski. He’s best friends with the series’ main character, Scott McCall (Tyler Posey). 

Although Stiles doesn’t have supernatural abilities like many other characters, he’s known for his quick wit, intelligence, and loyalty. As the series progressed, Stiles became central in helping Scott and others navigate various supernatural threats. Stiles Stilinski’s love interest in the show was Lydia Martin (Holland Roden). Teen Wolf aired originally for 6 seasons from June 5, 2011, to September 24, 2017.

4. American Assassin

 

The 2017 American Assassin movie was based on Vince Flynn’s 2010 novel. It cast Dylan O’Brien as Mitch Rapp, a young man seeking revenge after his fiancée is killed during a terrorist attack. Co-starring alongside Michael Keaton and Sanaa Lathan, O’Brien’s Rapp is recruited by the CIA and trained as a counter-terrorism operative. He is trained by ex-United States Navy SEAL and CIA agent Stan Hurley (Keaton). Dylan O’Brien delivered a believable performance as a highly-skilled, driven, and emotionally complex character. He effortlessly evolves from a vengeful civilian into a lethal government operative.

3. Love and Monsters

 

Dylan O’Brien led the cast of the 2020 monster adventure movie Love and Monsters. He played Joel Dawson, a young man living in a post-apocalyptic world where giant mutated creatures roam the Earth. He’s one of the few living humans who survived an asteroid fallout. During the ensuing panic, he’s separated from his High School girlfriend, Aimee (Jessica Henwick). 

Joel Dawson has been living in an underground bunker with other survivors for seven years. After receiving a radio message from Aimee, Joel decides to leave the safety of the bunker to reunite with her. With Aimee living in a colony 85 miles away, Joel decides to take the perilous journey across the monster-infested cities. In his journey, he encounters two survivors, Clyde (Michael Rooker) and Minnow (Ariana Greenblatt), who assist him.

2. Deepwater Horizon

 

In the Mark Wahlberg-led biographical disaster movie Deepwater Horizon, Dylan O’Brien was cast in a supporting role as Caleb Holloway. With the movie based on factual events, O’Brien’s Holloway was one of the Deepwater Horizon oil rig workers. His character is portrayed as one of the survivors, contributing to the movie’s plot bravery and harrowing experiences of the crew. Deepwater Horizon also starred Kurt Russell, John Malkovich, Gina Rodriguez, and Kate Hudson. Although a Box Office flop, the movie generally received positive reviews.

1. Maze Runner Trilogy

Dylan O'Brien in Maze Runner Trilogy

Dylan O’Brien’s biggest film project has been the Maze Runner trilogy. He played the series’ protagonist, Thomas, who woke up in a mysterious maze without a memory of his past. He becomes the last male to enter the Glade and leads a group of teens as they try to escape the maze and uncover the truth behind their captivity. 

O’Brien first appears in the first installment in 2014, reprising the role in its two sequels, Maze Runner: The Scorch Trials (2015) and Maze Runner: The Death Cure (2018), respectively. O’Brien co-starred alongside Kaya Scodelario, Thomas Brodie-Sangster, Ki Hong Lee, Will Poulter, Giancarlo Esposito, Dexter Darden, Aidan Gillen, Nathalie Emmanuel, and Walton Goggins. Besides these Dylan O’Brien top performances, check out Catherine O’Hara’s top memorable roles.

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