A Look at Kieran Culkin's Best Roles That Set Him Up for Succession

Kieran Culkin shed the title of "Macaulay Culkin's little brother" with a series of intriguing acting choices long before landing the role of Roman Roy on Succession.

By Natalie Finn Sep 30, 2022 12:00 PMTags
Watch: Kieran Culkin Talks "Succession" at 2022 SAG Awards

Oh, the Romanity.

Even if Succession can't last forever, who else wishes the parade of Roman-Royisms could go on in perpetuity? Kieran Culkin brings such poetry to lines like "We do roller coasters and hate speech" and "Hey, hey, motherf--kers!"

Which is why, even though he was originally called in to read for the part of Cousin Greg, who endearingly stumbles over every word, Kieran requested a tryout for Roman, who—at least in the beginning—is all talk. 

"I liked his voice, and I really clicked with it," the two-time Emmy nominee recalled on the Los Angeles Times podcast The Envelope in February. "Pretty much every syllable was like, I completely understand who this guy is, and that almost never happens. But I cannot tell you exactly what that is."

His personal connection to the wry, wounded Roman aside ("I'm still trying to find a therapist," he cracked), when he got the call he was ready, having stealthily honed his acting chops for years on parts that required a certain jaded but sensitive, sarcastic but intelligent affect with a dash of nervous energy.

Succession Season 3: The Best Burns

Or maybe that's what Kieran has always brought to the table, ever since he was refusing to go easy on the Pepsi in Home Alone, a movie he didn't even realize Macaulay Culkin was the star of until long after it was made.

Like his big brother, Kieran has been onscreen since he was a little kid, plying his trade for most of the past four decades, crossing the bridge from child star to busy grown-up actor. In honor of his 40th birthday Sept. 30, here's a look at the roles that set Kieran up for Succession:

Home Alone

Kieran Culkin made his movie debut at 7 playing Fuller, the rubber sheet-requiring little cousin of Macaulay Culkin's Kevin McCallister in the 1990 blockbuster that made the elder Culkin brother a full-fledged star and put Kieran on the map.

"I didn't even know what the movie was about when we were doing it," Kieran said on the Late Late Show With James Corden in 2020. "There's a part in the movie where there's a kid who gets his head counted incorrectly and he goes, 'Bye, bring me back something French!' I thought the movie was about that kid."

Only the Lonely

Kieran teamed up again with Macaulay in this 1991 John Candy comedy, this time the two playing brothers in director Chris Columbus' follow-up to Home Alone.

Father of the Bride

Brother-of-the-bride Matty Banks helpfully pointed out that no one wants to see the word "pit" on a wedding invitation in the 1991 classic. Kieran returned for the 1995 sequel and the mid-pandemic 2020 virtual reunion.

Nowhere to Run

In 1993, a single mother of two in distress couldn't do much better than having Jean-Claude Van Damme as her savior, as he was in one of the countless solitary-beefcake-saves-woman-from-human-or-machine-villain movies that were so popular at the time. Rosanna Arquette played a widow whose farm was under threat from ruthless contractors, Kieran was her son and the Muscles From Brussels was the escaped convict who makes everything right.

My Summer Story

So...there was a sequel to A Christmas Story and this 1994 family comedy was it, also directed by Bob Clark and based on Jean Shepherd's stories but starring Kieran as Ralphie Parker and Charles Grodin and Mary Steenburgen as his parents. Once again, there's a bully to be vanquished, but without the snow.

Youngest Culkin sibling Christian also joined the family as Ralphie's little brother Randy, and it's his sole acting credit.

The Mighty

Sharon Stone played Kieran's mom in this heartwarming tearjerker about two misfit kids whose friendship gives them the inner superpowers they need to get by in their small town.

She's All That

Kieran played younger brother Simon to Rachael Leigh Cook's social outcast-turned-potential-prom-queen Laney Boggs in the 1999 teen classic.

The Cider House Rules

Also in 1999, Kieran joined Tobey Maguire as resident "Princes of Maine" and "Kings of New England" in the orphanage-set drama that resulted in Oscar wins for John Irving's screenplay and supporting actor Michael Caine.

Igby Goes Down

In 2002 Kieran earned his first Golden Globe nomination for acting in a comedy for his turn as the titular New York rich kid dealing with an institutionalized father (Bill Pullman), an alcoholic mother (Susan Sarandon), an Alex P. Keaton-type brother (Ryan Phillippe), a mad crush on a girl (Claire Danes) and an affair with a woman (Amanda Peet) who's already the trophy mistress of his real estate tycoon godfather (Jeff Goldblum).

It's a hoot, albeit a dark one.

The Dangerous Lives of Altar Boys

The Catholic school travails of four friends growing up in Savannah, Ga., in the 1970s drive the coming-of-age action of this 2002 dramedy based on Chris Fuhrman's inspired-by-his-real-life novel of the same name.


Martin Scorsese executive-produced this 2008 drama-with-humor starring Rory Culkin as Scott, a sweet 15-year-old in 1979-era Long Island who's in love with his neighbor Adrianna, played by Emma Roberts. Life gets complicated when Adrianna's dad (Timothy Hutton) is diagnosed with Lyme disease and her mother (Cynthia Nixon) starts having an affair with Scott's father (Alec Baldwin). Meanwhile, his older brother Jimmy (Kieran), already no fan of their dad, is over all the parental hypocrisy.

Scott Pilgrim vs. the World

Kieran plays one of the few people Michael Cera doesn't have to battle in the 2010 cult-classic based on a graphic novel series. But upon closer inspection, Scott's roommate Wallace Wells is giving strong doesn't-give-AF-but-still-endearing Roman Roy vibes, only with much less profanity.


Kieran plays Paul, a slacker schoolmate of the interminably self-centered Margaret (Anna Paquin) who decides Paul's the guy she should lose her virginity to while also obsessively trying to atone for a bus accident she helped cause.

The real news, however, is that J. Smith-Cameron—Gerri, the object of Roman's twisted affection on Successionplayed Margaret's mom in the very long film directed by Cameron's husband, Kenneth Lonergan.


He isn't around for long, but Kieran had a memorable turn on the second season of Fargo as Rye Gerhardt, a junior member of a murderous crime family, whose hit-and-run death in the season premiere triggers much of the ensuing action. (Though, more accurately, Rye is hit and Kirsten Dunst's Peggy Blumquist calmly drives home with him still embedded in her windshield.) 

No Sudden Move

Kieran's gangsters don't have much luck. It's kill or be killed on the job in this Steven Soderbergh-directed all-star crime saga from 2021, and his character is, well...



Kieran has won two Critics' Choice Awards and been nominated for two Emmys and three Golden Globes for his pitch-perfect turn as the remarkably crass and calculating but obviously-in-need-of-a-hug Roman Roy, the youngest of Logan Roy's 3D-chess-playing heirs. 

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