10 Kieran Culkin roles that prove Roman Roy wasn’t a fluke

Kieran Culkin is no longer just that guy from Succession. He is now an Academy Award-winning actor. His searing performance as Benji Kaplan in A Real Pain earned him the Oscar for Best Supporting Actor this year. And honestly? About time! For those who have been tracking his career, Culkin’s win feels less like a “surprise” and more like Hollywood finally catching up.

Yes, Kieran Culkin's Roman Roy in Succession may have launched him into the pop culture stratosphere, but Culkin’s been quietly and consistently delivering standout performances for decades. He has played smart-mouthed sidekicks, emotionally fractured loners, deadpan scene-stealers, and everything in between. That sharp tongue, those wounded eyes, the chaotic charisma - it didn’t just appear in HBO’s boardrooms. Kieran Culkin as Roman wasn’t lightning in a bottle, he was the culmination of years of indie gems, offbeat comedies, and character-driven dramas where the actor proved again and again that he could bring nuance to even the most outrageous roles.

So, let us rewind. Who was Kieran Cullkin before he was Roman Roy? These 10 roles tell us that story!

10 Kieran Culkin roles that prove Roman Roy wasn’t a fluke

1) Igby Slocumb - Igby Goes Down (2002)

This might be the ultimate 'Roman-before-Roman' role in KIeran Culkin's career. As the rebellious Igby, Culkin plays a sarcastic, upper-class teenager with mommy issues and a disdain for the system. Sound familiar? It is practically Roman’s origin story. However, this performance isn’t just an early sketch of a future Roy. Kieran Culkin gives Igby a depth that is both tragic and hilarious. He earned a Golden Globe nomination for this role, and honestly, it still holds up as one of his best.

2) Scott Pilgrim’s roommate Wallace - Scott Pilgrim vs. The World (2010)

In a movie packed with quirky characters and comic-book visuals, Kieran Culkin somehow manages to steal scenes as the effortlessly cool, blunt, and delightfully sarcastic Wallace Wells. He is the kind of character who always knows what is going on and doesn’t care about your feelings while telling you the truth - basically, Roman Roy in a Canadian hipster world. The comedic timing here is immaculate, and every one-liner hits harder than Scott's bass drops.

3) Matty Banks - The Cider House Rules (1999)

Long before he was playing power-hungry media heirs or chaotic roommates, Kieran Culkin played Matty, a young orphan in this Oscar-winning drama. It is a small role, but he makes it memorable, showing early flashes of emotional nuance. Even as a kid, Culkin had that uncanny ability to play vulnerability without making it sappy. If you squint hard enough, you will see a future Roman buried beneath that mop of 1940s hair.

4) Neil – Music of the Heart (1999)

In this drama starring Meryl Streep, Kieran plays Neil, one of the kids learning violin in an inner-city music program. It’s a smaller role, but Kieran Culkin's earnestness shines through even in limited screen time. What’s remarkable is how grounded he feels - no generic child actor energy, just genuine emotion. It’s an early look at the vulnerability and sincerity that would later make his portrayal of Roman Roy so much more than just punchlines and power plays. Seeing him hold his own in a film packed with seasoned actors? A quiet flex!

5) Charlie Banks - Lymelife (2008)

Dark, moody, and soaked in suburban dread, Lymelife gave Culkin a rare opportunity to play the older, more stable brother - a big departure from his usual manic energy. Charlie is introverted, wounded, and just trying to make sense of his crumbling world. The restraint in this performance is impressive, proving Kieran Culkin doesn’t need rapid-fire quips to captivate. But don’t worry, he still finds moments to drop that classic Culkin cynicism.

6) Bobo - Movie 43 (2013)

Okay, hear us out - Movie 43 is…a lot! It’s chaotic, crude, and borderline nonsensical - but Kieran Culkin shows up for his segment like he’s starring in Shakespeare. As a fast food cashier in a wildly inappropriate sketch, he goes full deadpan absurdist, proving he’s not afraid to get weird (or deeply uncomfortable) for a laugh. Is it high cinema? No. But does it show his commitment to the bit? Absolutely.

7) Tucker - Quitters (2015)

Another under-the-radar gem, Quitters features Kieran Culkin as a chain-smoking, emotionally detached teacher who gives off serious "I peaked in college" vibes. He’s the kind of character Roman would’ve hated in high school, but probably ended up having drinks with later. There’s something hypnotic about Culkin in this role: the apathy, the flashes of misplaced passion, and that ever-present edge of self-loathing. It’s a vibe.

8) Simon - Margaret (2011)

This sprawling drama from Kenneth Lonergan is packed with powerhouse performances, and Kieran Culkin holds his own in a relatively small role as Simon, a classmate with romantic entanglements and emotional baggage. The scenes are intense, awkward, and brimming with unspoken tension - something Kieran thrives in. His ability to live in the silences makes even the smallest scenes impactful. It’s a far cry from Roman’s boardroom antics, but no less compelling.

9) Blaine - Go Fish (2001)

This American Sitcom gave Culkin a chance to be weird, sad, and weirdly sad in the best way possible. Playing a lonely kid in search of friendship, he delivers a performance that’s far more introspective than most actors his age could’ve pulled off. It’s a time capsule of his potential: all that emotional rawness just waiting to erupt into something as iconic as Roman Roy years down the line.

10) Roman Roy - Succession (2018–2023)

We’ve arrived! The role that redefined Kieran Culkin’s career and turned him into a household name (at least in homes that subscribe to HBO). Roman Roy is a masterclass in contradiction: arrogant yet insecure, hilarious yet heartbreaking, loyal yet sabotaging. Culkin brings layers upon layers to every smirk, quip, and breakdown. He didn’t just play Roman, he embodied him. Watching his arc from Season 1’s immature jokester to Season 4’s emotionally shattered man-child is like witnessing an actor go supernova in real time.

Kieran Culkin didn’t luck into Roman Roy, he earned him. These roles are proof that he’s been sharpening his tools for years, perfecting that razor-sharp blend of humor, humanity, and chaos. Roman wasn’t a fluke, he was the inevitable result of an actor who’s always known how to walk the fine line between brilliance and breakdown.