It’s often said that talent runs in the family, and the history of entertainment is filled with many popular dynasties of entertainers.Families like the Coppolas, Barrymores, Marshalls, Baldwins, Cusacks, Fondas, and Stillers have many members that are involved in the industry, and the same could be said of the Culkins. While it’s Macaulay Culkin’s iconic performance as Kevin McCalister in the 1990 holiday classicHome Alonethat launched the entire family into stardom, his younger brothers Kieran and Rory have had equally interesting careers. In recent years,Kieran Culkinhas emerged as one of the best character actors of his generation.
Culkin’s first role may not have been a huge challenge, as he was cast as the onscreen younger cousin of Kevin McCalister in bothHome Aloneand its 1992 sequelHome Alone 2: Lost in New York. However, Culkin soon proved that he was much more than just a friendly child star. He started appearing in many under-the-radar independent films that showed his growth as an actor before landing one of the lead roles on HBO’s wildly popular drama seriesSuccession.
Culkin’s scene-stealing performance as the petulant Roman Roy has recently earned him a Primetime Emmy Award and Golden Globe for Best Actor, and he’s emerged as one of the fan-favorite characters on the series. His most recent film, A Real Pain, just held it’s world premiere at the 2024 Sundance Film Festival and audiences are eagerly awaiting his next release. Here are the best-ranked Kieran Culkin movies and TV shows.
Update July 26, 2025: This article has been updated following Kieran Culkin’s incredible awards win run for his role onSuccessionand following the premiere ofA Real Painat the Sundance Film Festival.
10Home Alone (1990)
Culkin got his first taste of stardom when he appeared alongside his brother Macaulay in the originalHome Alone. While he doesn’t have a major role, it’s interesting to see the two brothers bicker and squabble in the opening scenes, perhaps drawing from their own childhood experiences.
The Brothers Share the Big Screen
It was fun for audiences to watch the two Culkins team up for thebeloved holiday classic, with the younger brother’s character Fuller McCallister hamming it up for the camera despite his limited screen time. Kevin’s bed-wetting cousin Fuller also returned for the highly-anticipated follow-upHome Alone 2: Lost in New York,and when asked if he was able to enjoy the Christmas hit like the rest of the world,Culkin told Entertainment Tonight,“Absolutely. Every Christmas that’s just on. I think we used to watch it a bunch even as a kid, so it just has that same sort of nostalgia.“Stream onDisney+
9Fargo (2015)
Although fans of the Coen Brothers may have feared that anything related to the1996 filmFargowould never live up to the original classic, the FX series, also calledFargo, has the same quirky mixture of crime, comedy, emotion, and existentialism. Culkin plays one of the many ill-fated characters in the show’s excellent second season, with the actor working alongside famous faces like Kirsten Dunst, Jesse Plemmons, and Patrick Wilson.
Related:The 10 Best Episodes of the Fargo TV Series, Ranked
Culkin’s Complex Portrayal
Culkin gives a sniveling, yet strangely sympathetic performance as Rye Gerhardt, the youngest child of a crime family whose death sets off the gang conflict in the season. Despite wanting to desperately take over the family business, Rye realizes he will never rise in ranks and instead decides to break away and create a criminal empire of his own, leading to a grim fate for the character. Though he was only in two episodes, Culkin was able to show off his range and star power as an actor.Stream onHulu
8The Cider House Rules (1999)
The intimate 1999 drama,The Cider House Rules, stars Tobey Maguire as the young student Homer Wells as he grows up in a New England orphanage and becomes a student to veteran doctor Dr. Wilbur Larch,played by Michael Caine. The performance won Caine his second Academy Award for Best Supporting Actor, and the engrossing film also nabbed the statuette for the highly prestigious Best Adapted Screenplay.
Wise Beyond His Years
Culkin gives one of his more sensitive performances as Buster, an older orphan who helps Homer watch over the young children and offer them guidance during troubling times. The up-and-coming actor shined alongside seasoned Hollywood veteran Caine, and his effortless on-screen camaraderie with Maguire was without-a-doubt one of the drama’s most touching relationships and helped deliver plenty of heart.Rent/Buy onPrime Video
7Father of the Bride (1991)
Father of the Brideis one of the most hilarious family comedies of the 1990s, as it successfully shows all the stress, planning, and turbulent emotions that are involved with a wedding.The great Steve Martinheadlines the beloved romantic comedy, portraying a devoted father and husband who struggles with the impending nuptials of his recent college graduate daughter (Kimberly Presley).
A Fan-Favorite Franchise
In one of his earliest roles, Culkin proved he could act alongside comedic legends with his performance as Matty, the young son of Martin’s George Stanley Banks. Following in the footsteps of his older brother Macaulay, Kieran established himself as quite the talented kid and showed off his funny bone in the endearing flick, and reprised the role for the 1995 follow-up. Fans of the franchise were elated when the cast membersreunited via Zoomin 2020 for the short sequelFather of the Bride, Part 3(ish), with Culkin serving up some laughs alongside the Banks family once again.Stream onDisney+
6The Dangerous Lives Of Altar Boys (2002)
One of Culkin’s best films is also sadly one of his most underseen;The Dangerous Lives of Altar Boyswas a box office disappointment despite strong reviews for Culkin’s performance. He stars as Tim Sullivan, a Catholic schoolboy who struggles to adjust to the conformity of his upbringing by imagining wild cartoons of comic book heroes, villains, and powers. Culkin is joined by stars like Emile Hirsch, Jodie Foster, and Vincent D’Onofrio in the underrated flick in an adaptation of the inspiring coming-of-age novel.
A Heartfelt Adaptation
The Dangerous Lives of Altar Boysis based on the semi-autobiographical work by Chris Fuhrman, and filmmakers felt that Culkin had a similar personality to his counterpart Tim, with producer andco-star Foster statingat the time, “I think he is going through a lot of similar things [in his own life].” The dramedy features exceptional performances by its star-studded cast and despite failing to make waves at the box office, it went on to win the Independent Spirit Award for Best First Feature.Stream onVudu
5No Sudden Move (2021)
Read Our Review
Steven Soderbergh never fails to put together an incredible ensemble cast, but the list of great actors that pop up in his 2021 crime thrillerNo Sudden Moveis just absurd. Benicio del Toro, Don Cheadle, and Brendan Fraser are just a few of the illustrious stars that appear in the gripping picture, which follows a group of small-time criminals who discover they have been double-crossed by a mysterious presence and must figure out who wants them dead.
Related:Steven Soderbergh’s 10 Most Underrated Movies, Ranked
Culkin Embraces His Dark Side
Culkin still manages to leave an impact in this 1950s set heist film with his uncharacteristically depraved performance as the vile hitman Charley. It was an effective bit of casting against type that gave Culkin the rare chance to play the villain, and he more than rose to the occasion as the violent and depraved killer. Upon its premiere at the Tribeca Film Festival,No Sudden Movegarnered widespread praise for its many twists-and-turns and superb acting, and was streamedby 567,000 householdswithin its first four days on Max.Stream onMax
4Margaret (2011)
Kenneth Lonergan’sMargaretis a modern masterpiece that explores the existential grief of the teenage girl Lisa Cohen (Anna Paquin) in the aftermath of a tragic bus accident that she feels responsible for. Culkin plays her love interest Paul Hirsch, a charming yet clueless classmate who can’t begin to understand why Lisa is so emotionally distant during their intimate romantic encounter.
Well Worth the Wait
Despite being filmed back in 2005,Margaretwasn’t released until 2011 because director Kenneth Lonergan had difficulty creating a final cut he was pleased with. Martin Scorsese and Thelma Schoonmaker even helped edit a 165-minute version of the drama, which was rejected by its producer, Gary Gilbert, and subsequently caused it to remain in cinema limbo. Nonetheless, the psychological drama has gone on to receive critical appreciation in the years since its release, with many considering it one of thefinest films of the decade.Rent/Buy onApple TV+
3Scott Pilgrim vs. the World (2010)
Culkin proved once again inScott Pilgrim vs. the Worldthat no matter how stacked the cast is, he could always be the scene stealer. Michael Cera stars as the eponymous musician, who embarks on a noble quest to not only land a coveted record deal but also takes on his new lady love Ramona Flowers' (Mary Elizabeth Winstead) evil ex-boyfriends.
Culkin’s Scene-Stealing Performance
Wallace is the hilarious roommate of Scott (Michael Cera) who does everything that a best friend should; he covers for Scott during embarrassing moments, cheers him on during the action scenes, and gives him frank, unsentimental advice about his incompetent love life. Of course, seeing Wallace flirt with any younger man he finds attractive is absolutely hilarious.Scott Pilgrim vs. the Worldalso touts a fantastic soundtrack and has won numerous accolades, like an Empire Award and two Satellite Awards, including Best Motion Picture. Culkin also reprised his role in the 2023 anime sequel/reimaginingScott Pilgrim Takes Off.Stream onNetflix
2Igby Goes Down
Igby Goes Downis quite simply one of themost underrated moviesof the 21st century. In a performance that is both hilarious and heartbreaking, Culkin stars as the wealthy teenager Igby Slocumb who attempts to escape his ultra-privileged life and his domineering mother Mimi (Susan Sarandon) by venturing off into New York City to join the bohemian artists.
A Poignant & Captivating Portrayal
Igby’s rebellious nature stems from a challenging childhood and the absence of his schizophrenic father (Bill Pullman), but he uses his unparalleled wit to mask his emotions. Igby mistakes his sense of irony for maturity as he’s forced to grow up in world where he has to take things seriously every now and again. Both Culkin and Sarandon earned Golden Globe nods for their complex performances, withRoger Ebert commendingthe star: “Kieran emerges here as an accomplished, secure comic actor with poise and timing…He is not simply a rebellious, misfit teenager with a con man’s verbal skills, but also a wounded survivor of a family that has left him emotionally scarred.“Rent/Buy onPrime Video
1Succession (2018 - 2023)
Culkin’s later career got a major rush of adrenaline with his incredible performance as Roman Roy on HBO’s smash hitSuccession. Although the insults and crude remarks that fly out of Roman’s mouth are generally hilarious, he’s secretly one of the most complex characters in the series, which centers on theinfluential Roy familyas they run their massively successful New York City company.
A Decorated Television Tenure
Roman is haunted by the bullying he received from his father Logan (Brian Cox) when he was younger and forms an odd attachment to the elder RoyCo employee Gerri Kellman (J. Cameron Smith). Their unusual relationship becomes a genuine partnership as Roman shifts sides during the climactic family duels, and Culkin proves himself to be one of the industry’s most dynamic and understated performers with the career-defining role. For his exceptional work inSuccession, Culkin rightfully earned three Screen Actors Guild Awards and recently took home both a Golden Globe and Primetime Emmy following the show’s conclusion. This has now become his most defining roles and the one that will define his career.Stream onMax
