From a hero trapped in a maze to a pair of clout-chasing influencers, Dylan O’Brien has a wide range of movie roles behind him. Beginning his road to stardom by uploading a number of his own video shorts to YouTube, and gaining the attention of a manager, it was O’Brien’s role as Stiles Stilinski on the MTV series Teen Wolf that solidified his talents. Portraying the nebbish best friend to Tyler Posey’s Scott McCall, and continuing the teen drama archetype familiar to viewers of Buffy the Vampire Slayer and The OC, O’Brien quickly made the character his own – a sardonic high school student exuding warmth and bravery as often as he’s supplying snarky one-liners.
Director Kevin Smith observed Dylan O’Brien as a promising acting talent when he interviewed the actor for a podcast only a month after Teen Wolf‘s debut, predicting that O’Brien would have a thriving career. More than a decade after his breakout performance as Stiles, that’s proven to be correct. In the intervening years, O’Brien’s audience continues to fervently support his projects and root for him to take the next step in becoming a household name. This has made the New York native a popular choice for superhero fancastings, as Dylan O’Brien is frequently suggested for Nightwing, The Flash, and even Spider-Man.
For his part, Dylan O’Brien has a more understated perspective on his acting career. Back in 2017, he explained to The Los Angeles Times that he would rather have a smaller profile and a smaller career while still being able to work on productions that mean something to him. It’s a stance he’s reiterated since, noting that he has no interest in lining up several movies each year for the sake of it. That selectiveness hasn’t precluded a few blockbusters from sneaking into his filmography. But it’s also helped to bring about some of his very best work, which highlights the amiability and energy that makes actor Dylan O’Brien a uniquely enjoyable screen presence. Here’s every feature-length Dylan O’Brien movie ranked from worst to best.
14. American Assassin (2017)
The most interesting aspect of American Assassin is the degree to which it plays out like a spy thriller from a bygone era. Michael Cuesta’s adaptation of Vince Flynn’s novels starts with a young woman who is on-screen just long enough to die in a terrorist attack. It’s included for the sole purpose of fueling the protagonist’s quest for vengeance, and this proves to be a running theme throughout. Women, both minor and somewhat more significant, are killed off unceremoniously but not before the camera takes a few moments to leer at their bodies. The politics, more broadly, are even worse. The action movie has its most appalling scene see the ostensibly heroic Mitch Rapp (O’Brien, exuding intensity in a movie that requires little else) decide to torture a character based largely on the fact that she’s Iranian. It would be one thing if the adaptation was entertaining and inventive with its action despite its glaring flaws – but American Assassin fails in this regard, too. It begins as an exploitive though fairly direct revenge story, ballooning into a numbingly incomprehensible mess by the end in hopes of a franchise that never materialized thanks to lackluster box office tally and tepid reviews.
13. Infinite (2021)
If there’s a positive to be taken from the futuristic Infinite, it’s that O’Brien’s brief appearance at the start of the film constitutes its best portion. Racing through streets and evading cop cars to the tune of “Legends Never Die” by Campfire, O’Brien’s propulsive and dynamic cameo as the sword-wielding Heinrich Treadway led both critics and general audiences to argue that he would have been a better fit for the main role. To be fair to Mark Wahlberg’s leading performance, he’s not the only problem with this book adaptation. It’s also that the rest of the Infinite timeline – which centers around the factional battle between groups of people with perfect memory of their past lives – never again comes close to matching its promising prologue. As the director, Antoine Fuqua can’t quite liven up a story that settles into uninteresting incoherence and shrugging imitations of far superior sci-fi movies like The Matrix.
12. Flashback (2021)
First announced in May 2018, with shooting wrapping up by October, Flashback would take three years and a few title changes before reaching audiences. It’s an understandable delay for O’Brien’s most genre-heavy and alienating project to date. He plays Fred, a man who considers himself lucky enough to be in a stable job and a loving relationship as he turns 30. Still, when a high school classmate (portrayed by Maika Monroe) goes missing, Fred begins to descend into a world of mind-altering drugs that leaves him questioning his own reality and forces him to reevaluate every choice he’s made. To reveal anything more specific would spoil Flashback. Or it would – if the thriller movie was, in any way, easy to follow. Christopher MacBride, as the writer and director, crafts a narrative that is more focused on inviting viewers to ask questions than allowing for anything to land with emotional resonance.
It works in a sense. For those interested in unfurling Flashback’s myriad mysteries, MacBride offers plenty to chew on. But it comes at the cost of the story and the performances. Dylan O’Brien gets to play around with big emotions, arguably the biggest of any of his films, but it’s in service of a protagonist that never evolves past being a cipher. Monroe, a revelation in thrillers like The Guest and It Follows, is even less fortunate. Her character, Cindy, is reduced to the Troubled Dream Girl that Fred has to track down simply because the plot demands it.
11. High Road (2011)
Directed by Matt Walsh, with an improvisational script from Walsh and Josh Weiner, High Road begins with the disgruntled Jimmy (O’Brien) hanging out with his aimless older neighbor Fitz (played by James Pumphrey). Pressures pile up. And, before long, the unlikely pair find themselves on the run — with nowhere to go. There’s enough foundation in the premise, of Jimmy’s dysfunctional relationship with his father, and Fitz’s habit of avoiding any semblance of responsibility, that would make for a decent mismatched comedy on its own. In his debut movie role, actor Dylan O’Brien demonstrates a knack for humor and an easy rhythm with Pumphrey. Their characters alternate between bickering and working as a team, often in the span of seconds, and it’s held together by a reasonably affecting undercurrent about two grieving screwups that are more alike than they realize. With a little more focus on the duo, who only share the screen for less than half of the runtime, rather than a scattered set of supporting players, High Road might’ve been worth a stronger endorsement.
10. Deepwater Horizon (2016)
Directed by Peter Berg, and depicting the real explosion of the Deepwater Horizon drilling rig and the initial oil spill in the Gulf of Mexico, the eponymous film has a certain appeal in how it shows the workers going about their jobs unglamorously and debating standards of safety on what looks to be a dangerous endeavor. That approach becomes less palatable the longer Deepwater Horizon goes on, when it becomes clear that the plain storytelling is as much a stylistic choice as it is a lack of interest in the humans at the center of the disaster and the calamitous environmental impacts of the spill. The characters are perfunctory, like Mark Wahlberg’s family man who just wants to get back home. Or in the case of John Malkovich, who portrays a cowardly BP manager, they’re cartoon villains that are used as scapegoats for the failures and the greed of an entire industry. Others in the cast, like O’Brien, don’t even get that much to work in the short time that they’re on-screen.
When the explosion occurs, it’s admittedly impressive. It’s a blazing, sweat-soaked, and muddy finale that’s appropriately bracing. The tension is showcased through visuals of ceaseless flames and flying shards of glass and also through booming sound design – a category that garnered nominations for Deepwater Horizon at both the Academy Awards and the BAFTAs. It’s a fine disaster film, in other words. But when that disaster is so devastating on a multitude of levels, it’s difficult not to wish for something more substantive.
9. The First Time (2012)
After meeting each other at a party and falling in love over the course of a weekend, high school students Dave Hodgman (O’Brien) and Aubrey Miller (Britt Robertson) decide that they’re ready to have sex. Both teens are jittery. They pace around, stammering, and initiating random topics of conversation as a way of stalling an experience they should be so excited to share. For all the hype, for as much as they’ve built up the milestone in their heads, their first time winds up being a distinct disappointment.
At its best, Jonathan Kasdan’s The First Time is refreshingly realistic in its depiction of romantic comedy movie hallmarks. This is evident at the moment which gives the film its title, but it also comes through during Aubrey and Dave’s initial encounter. Stretched out for over 20 minutes, and echoing Richard Linklater’s Before Sunrise trilogy, two strangers who aren’t quite sure of themselves attempt to forge a connection. More often, as is the case with Kasdan’s similarly deflating In The Land of Women, this romcom settles for the modest spark between its leads and plenty of the genre’s tired tropes: the silent Black friend, the one-dimensional villain, and the underserved supporting female character.
8. The Maze Runner (2014)
The Maze Runner might be O’Brien’s biggest movie role so far, giving him the opportunity to headline a franchise and exposing him to a worldwide audience in the process, but it’s hard to argue that his first outing as Thomas counts as his most exciting performance. As the main character in Wes Ball’s adaptation of James Dashner’s young adult dystopian novels, Dylan O’Brien functions as a surrogate for the audience. He’s the neutral hero, asking questions the viewers would ask, and pressing for answers. This function leaves little room for O’Brien to imbue his protagonist, Thomas, with any sense of interiority or pathos. It’s a plot-centric portrayal that is, although perfectly solid, more about moving the story forward. Will Pouter and Thomas Brodie-Sangster as the antagonist of the film and the reluctant leader, respectively, fare better. They’re each afforded more definition from the jump.
The Maze Runner, on the whole, is a similarly mixed bag. Ball, along with screenwriters Noah Oppenheim, Grant Pierce Myers, and T.S. Nowlin, does a good job of building up a sense of intrigue and mystery around the premise. And to its credit, the film avoids some of the prevalent YA clichés. Still, as it draws closer to its conclusion, the careful world-building is abandoned in favor of fights with giant CGI spiders and a blatant cliffhanger for the next installment.
7. The Internship (2013)
For a movie that plays like an extended advertisement for Google, with scenes frequently pausing to heap praise on the tech giant, The Internship is a kindhearted comedy which proves surprisingly hard to dislike outright. A lot of the credit goes to Vince Vaughn and Owen Wilson, reuniting after 2005’s smash hit Wedding Crashers to play a pair of two clueless salesmen that find themselves vying for a full-time job at Google in the comedy movie. It makes for a more mild story than their previous collaboration, and one that’s not nearly as funny, but their performances are still winning. Credit goes, as well, to the supporting cast and, especially, to O’Brien. As the scene-stealing and sharp-tongued Stuart, the actor refers to Vaughn as a “big tree” at one point. Delivered with a mix of exasperation and bewilderment, it’s among the best line readings of O’Brien’s career.
6. Maze Runner: The Scorch Trials (2015)
Staying true to its title, there is a lot of running in Maze Runner: The Scorch Trials. The second entry in Wes Ball’s trilogy sees the survivors of the first film fleeing frantically from danger, pausing for brief respites, and receiving exposition from well-known actors in supporting turns. It’s rigid a structure that repeats throughout the sequel, proving to be a trying experience for both the characters and viewers of the action sci-fi movie. Still, with a deliriously fun setpiece soundtracked by Patsy Cline’s “Walking After Midnight”, not to mention an early zombie attack in an abandoned shopping mall, The Scorch Trials has a few expertly-crafted action scenes which elevate it from its predecessor.
5. Bumblebee (2018)
Explaining the decision to choose O’Brien to cameo as the voice of the titular Autobot in Bumblebee, producer Lorenzo di Bonaventura praised the actor for bringing a level of trustworthiness and youthful exuberance to the character. Even though O’Brien is only heard in the film’s earliest scenes, it does prove crucial to setting the tone for one of the more widely-praised entries in the Transformers movie franchise. Operating largely as a standalone prequel, with Bumblebee seeking refuge on Earth, the movie is packed with entertaining showdowns between Autobots and Decepticons. It’s also sweetly nostalgic, as evidenced by Hailee Steinfeld’s heartfelt turn as the lead.
4. Maze Runner: The Death Cure (2018)
Sidestepping the common trend of splitting the final entry into two separate movies, Maze Runner: The Death Cure ends the franchise on a high note. Delayed for almost a year from its original release month of February 2017, due to the terrible injury O’Brien experienced while filming, the concluding chapter in the young adult saga opens with an intricate sequence and keeps the momentum going throughout the adaptation’s 143 minutes. Things occasionally get a little bloated, and the plot and the ending of Maze Runner: The Death Cure suffers a bit from the burden of having to tie up several loose ends. But in his best showing behind the camera, director Wes Ball evinces the right balance between thrilling action and the personal moments too frequently lacking from the previous two installments. O’Brien, no longer simply asked to move the plot forward, benefits greatly from this balance.
In the most enjoyable stretch of The Death Cure, the story shifts to something out of a heist movie as Thomas and his cohorts scheme to break out their friend from the heavily-secured building of the sinister WCKD corporation. It’s here, more than the previous Maze Runner movies, and certainly more than the woeful American Assassin, that O’Brien’s potential as an action movie star shines through. He’s quick on his feet and a little bit funny, tapping into the charisma that the franchise has never allowed him to show. But the script from T.S. Nowlin also affords Thomas the opportunity to briefly sit with all the trauma and loss he’s endured, with O’Brien selling the turmoil that had been building since his character was first introduced. The large ensemble of Maze Runner: The Death Cure all get their moments to shine, as well, as an uneven trilogy unquestionably sticks its landing.
3. The Outfit (2022)
O’Brien’s standout scene occurs early in The Outfit. His character, Richie Boyle, has a few moments to spend alone with trusty tailor Leonard Burling (Mark Rylance). Up to that point, viewers have witnessed how anxious Richie is – anxious to be taken seriously as a mobster, anxious to step out from his partner’s shadow, and anxious for his father’s approval. But when he feels as if he doesn’t have an audience to perform for, he lets his guard down. He laughs freely, listens respectfully, and expresses sincere gratitude to Leonard for his help. O’Brien does a lot in the short conversation, signaling Richie’s shielded vulnerability with just a downward glance or a calculated flare of his nostrils, and the gentle exchange is almost enough to make viewers forget that Leonard is being forced to assist Richie against his will.
Alternating between quiet conversations and chaotic confrontations proves to be The Outfit‘s greatest strength. Directed by Graham Moore, the mob story unfolds in the single location of Leonard’s shop. Although the tailor is used to dealing with his criminal clients, he finds himself roped into their heated rivalries one night. The script, co-written by Moore and Johnathan McClain, is smart enough not to treat Leonard as a poor old victim. Oscar winner Rylance never plays into that either, peeling back his protagonist’s layers while the circumstances grow steadily more dangerous. The setting is utilized equally as wisely, never coming across as constrained or contrived. Instead, The Outfit is something that feels increasingly rare: a well-made, breezy adult drama that is elevated higher by a cast that came to play.
2. Not Okay (2022)
After appearing as a dismissive and gaslighting boyfriend in the “All Too Well” short film, directed by Taylor Swift, Dylan O’Brien’s streak of playing against type continued with Not Okay. He plays Colin, covered in tattoos and shrouded in a cloud of vape smoke whenever he makes an entrance. Just a white guy from Maine – as one annoyed co-worker points out midway through the film – O’Brien appropriates a language and a presentation that’s not his own for the sake of clout. Elaborating on his inspiration for the role, O’Brien spoke of “white tatted kids who talk with blaccents as if they’re from the streets.” Again and again, up until the closing minutes, Not Okay leans on Colin’s patheticness for glorious comedic relief.
As loathsome as Colin is, he might not be the worst character in this sharp social media satire. That distinction goes to Danni Sanders (Zoey Deutch), a photo editor who lies about having survived a terrorist attack and gets the fame she always dreamed of as a result. Deutch, who worked with O’Brien on The Outfit movie, is fantastic. Her protagonist is rarely depicted in a sympathetic light, albeit Deutch still offers just enough to make viewers wish Danni would pull back before she falls completely into her unforgivable lies. Still, the true standout might be Mia Issac. The newcomer portrays Rowan Aldren, a school shooting survivor and activist that gets the celebrity and hollow hashtags she never asked for – but doesn’t get the legislation that would help to prevent tragedies like hers from happening again.
It’s that last part that makes Not Okay more than a mere showcase – for Isaac’s rousing rage, Deutch’s versatility, and O’Brien’s underutilized comedic chops. Writer-director Quinn Shephard helms her second feature with a light touch, while infusing her screenplay with biting ideas about how a capitalist society turns activists into commodities rather than address the specifics of their activists. It also touches on how the performance of trauma is similarly rewarded, even when that trauma is fabricated and easily disproven. It might seem like the commentary grapples with more than it handle, but a stunning ending, involving Rowan and Danni, cements the potential case for Not Okay as one of the best movies of the year.
1. Love and Monsters (2020)
There are several factors that combine to make Love and Monsters an underrated gem. Delayed due to the COVID-19 pandemic, and ultimately released on VOD, the film is a post-apocalyptic dramedy set in a world reeling from an unprecedented disaster that has left people struggling with how to move forward in their lives. But more than its unintended timeliness, the movie is a surprisingly beautiful and delightfully weird adventure that’s anchored by O’Brien in his career-best performance. The actor plays Joel Dawson, one of the relatively few survivors following a chemical catastrophe and a flawed response that has caused giant monsters to control what remains of Earth. Tired of being the only single person in his colony, and missing his girlfriend Aimee (played by Jessica Henwick), who he was separated from during an emergency evacuation seven years earlier, Joel decides to embark on a dangerous 85-mile journey in order to reunite with his former sweetheart.
Love and Monsters has plenty to recommend it, from director Michael Matthews’ refreshingly serene visualization of dystopia to the script, from Brian Duffield and Matthew Robinson, which wears its influences on its sleeve, and even the occasionally adorable monsters themselves. So much of the film’s success depends on Dylan O’Brien, though, who shares the bulk of his screentime with a stray dog and has the most emotionally resonant scene with a talking robot. It’s not quite a one-man show, but it comes close at times. So, it’s a good thing that the actor’s personality shines through from the very first seconds of the wry opening narration. Unlike most of The Maze Runner trilogy, which essentially sidelines O’Brien in favor of plot momentum, and American Assassin, which buries his natural charisma, Love and Monsters wisely leans all the way into the everyman quality that O’Brien embodies so well.
Perhaps the most surprisingly emotional scene takes place halfway through Love and Monsters. Joel happens on the robot, named Mav1s, and with its last minutes of battery power, sitting out in the rain, Mav1s gives Joel a chance to say goodbye to the mother he abruptly lost. The duo takes a moment, all too fleeting, to listen to “Stand by Me” as the night sky lights up with luminous jellyfish – but not before O’Brien conveys an immense sense of grief with as little as a crack of his voice and his slowly watering eyes. It’s more than some actors manage with whole pages of dialogue. Evocative and understated, the remarkable eight minutes clearly demonstrate what Dylan O’Brien can bring to a role. And as he holds steady to his goal of seeking out interesting projects, it promises a career that’s well-worth following.