Career Timeline of Dylan O'Brien: Major Achievements and Milestones

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Dylan O'Brien

Discover the career path of Dylan O'Brien, from the first major opportunity to industry-changing achievements.

Dylan O'Brien is an American actor who gained recognition for his role as Stiles Stilinski in the MTV series *Teen Wolf* (2011-2017). He further rose to prominence as the lead in the *Maze Runner* film trilogy (2014-2018), which opened doors to other film roles.

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2010: Cast in Teen Wolf

In 2010, Dylan O'Brien was cast as Stiles Stilinski in MTV's Teen Wolf after four auditions, marking a significant break in his acting career.

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2011: First Major Role in Teen Wolf

In 2011, Dylan O'Brien landed his first major role as Stiles Stilinski in the MTV supernatural series Teen Wolf.

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2011: Introduced in High Road

In 2011, Dylan O'Brien was introduced to audiences in the entirely improvised independent comedy film High Road.

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2013: Co-starred in The Internship

In 2013, Dylan O'Brien co-starred in the comedy film The Internship while on hiatus from Teen Wolf.

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2014: Lead Role in Maze Runner

In 2014, Dylan O'Brien achieved further prominence for his lead role in the science fiction Maze Runner trilogy.

September 18, 2015: Maze Runner: The Scorch Trials Release

On September 18, 2015, Dylan O'Brien reprised the role of Thomas in Maze Runner: The Scorch Trials.

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2016: Appeared in Deepwater Horizon

In 2016, Dylan O'Brien appeared in the disaster thriller-drama Deepwater Horizon, based on the 2010 Deepwater Horizon explosion.

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2017: Starred in American Assassin

In 2017, Dylan O'Brien played fictional counterterrorist Mitch Rapp in the action thriller American Assassin.

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2017: Teen Wolf Concludes

In 2017, the MTV supernatural series Teen Wolf, where Dylan O'Brien played Stiles Stilinski, came to an end.

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January 26, 2018: The Death Cure Premieres

On January 26, 2018, The Death Cure premiered, after Dylan O'Brien recovered from serious injuries sustained during filming.

2018: Maze Runner Trilogy Conclusion

In 2018, Dylan O'Brien concluded his lead role in the Maze Runner trilogy, leading to more film appearances.

2018: Filmed Flashback

In 2018, Dylan O'Brien filmed the mystery thriller Flashback, which was later released in 2020.

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2018: Voiced Bumblebee

In 2018, Dylan O'Brien voiced the CGI title character in the Transformers spin-off film Bumblebee.

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2019: Guest Starred in Weird City

In 2019, Dylan O'Brien guest-starred in the comedy sci-fi anthology series Weird City.

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2020: Lead Role in Love and Monsters

In 2020, Dylan O'Brien played the lead role in the adventure film Love and Monsters.

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2020: Starred in Flashback and Love and Monsters

In 2020, Dylan O'Brien starred in the mystery thriller Flashback (filmed in 2018), and the post-apocalyptic road trip film Love and Monsters.

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February 2021: Cast in The Outfit

In February 2021, Dylan O'Brien was cast in The Outfit, a film for which filming was completed in April 2021.

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April 2021: Filming completed for The Outfit

In April 2021, filming was completed for The Outfit, a film for which Dylan O'Brien had been cast in February 2021.

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August 2021: Cast in Not Okay and Caddo Lake

In August 2021, Dylan O'Brien was cast in Not Okay, for which filming finished in September 2021, and Caddo Lake.

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September 2021: Filming Completed for Not Okay

In September 2021, filming was completed for Not Okay, a film for which Dylan O'Brien had been cast in August 2021.

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October 2021: Guest Star in Curb Your Enthusiasm

In October 2021, it was announced that Dylan O'Brien would guest star in season 11 of Curb Your Enthusiasm.

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November 12, 2021: Starred in Taylor Swift's All Too Well

On November 12, 2021, Dylan O'Brien starred opposite Sadie Sink in Taylor Swift's short film All Too Well.

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2022: Credited as Drummer on Snow on the Beach

In 2022, Dylan O'Brien was credited as a drummer on the track "Snow on the Beach" from Taylor Swift's tenth studio album, Midnights.

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2024: Lead Role in Caddo Lake

In 2024, Dylan O'Brien played the lead role in the horror film Caddo Lake.

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2025: Critical Acclaim for Twinless

In 2025, Dylan O'Brien received critical acclaim for his lead role in the independent film Twinless.

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2025: Twinless wins Audience Award

In 2025, Twinless was screened at the Sundance Film Festival, where it won the Audience Award – U.S. Dramatic.

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2026: Starred in Send Help

In 2026, Dylan O'Brien starred in Sam Raimi's survival horror film Send Help, released in January.

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2026: Scheduled to Star in Being Heumann

In 2026, Dylan O'Brien was scheduled to star in Sian Heder's biographical drama Being Heumann.

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