See the Best Vintage Photos of the Culkin Siblings Together
See the Best Vintage Photos of the Culkin Siblings Together
Brendan LeTue, July 21, 2026 at 10:30 AM UTC
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Kieran and Macaulay Culkin
The Culkin siblings have each paved their own paths in Hollywood.
While Macaulay became a household name with his iconic role as Kevin McCallister in the Home Alonemovies, little brother Kieran had his breakthrough as Roman Roy in the Emmy-winning HBO series Succession. Their youngest brother, Rory, has also found success in films like Scream 4 and the acclaimed drama Columbus.
After Kieran won Best Supporting Actor at the 2025 Oscars, Macaulay told Entertainment Weekly at the Vanity Fair afterparty that he only watched the awards show to see his younger brother win.
“[Best Supporting Actor is] the only thing I watched,” the Golden Globe nominee admitted. “True story, true story… I cried. And I was like, ‘I’m gonna see you later.’ “
Macaulay, Rory and Kieran also have four more siblings: Shane, Christian, Quinn and their late sister Dakota, who died in 2008.
As Rory turns 37 on July 21, 2026, see the Culkin siblings’ sweetest throwback photos over the years.
01 of 13
Two in Tuxes
Macaulay and Kieran Culkin in 1991Credit: Ron Galella, Ltd./Ron Galella Collection/Getty
Macaulay and Kieran, then 10 and 8, suited up to attend the American Comedy Awards in Los Angeles.
02 of 13
Head Scratcher
Rory and Kieran Culkin in 2000Credit: Richard Corkery/NY Daily News Archive/Getty
A 10-year-old Rory brought older brother Kieran to the premiere of his movie You Can Count on Me in New York City.
03 of 13
Backstage Pass
Macaulay and Kieran Culkin in 2001Credit: KMazur/WireImage
Kieran and Macaulay were all smiles backstage at Michael Jackson’s 30th anniversary celebration show in N.Y.C.
04 of 13
Birds of a Feather
Kieran and Macaulay Culkin in 2001
Macualy rocked a black boa alongside Kieran at the afterparty of Serendipity’s New York premiere.
05 of 13
Star in Stripes
Kieran and Macaulay Culkin in 2002Credit: Jim Spellman/WireImage
The brothers looked like spitting images of each other at a charity premiere of Star Wars: Episode II - Attack of the Clones in New York City.
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06 of 13
Look Up to You
Rory and Kieran Culkin in 2002Credit: Dimitrios Kambouris/WireImage
Leading man Kieran and Rory, who plays the younger version of his brother’s character, stopped by a screening of Igby Goes Down in Southampton, New York.
07 of 13
A Little Push Back
Macaulay and Kieran Culkin in 2005Credit: Richard Corkery/NY Daily News Archive/Getty
Kieran starred in an Off-Broadway production of After Ashley, and his brother joined him at the opening night afterparty.
08 of 13
Award-Winning Smile
Kieran and Macaulay Culkin in 2005Credit: Richard Corkery/NY Daily News Archive/Getty
For his performance in After Ashley, Kieran picked up an Obie Award, and Macaulay was right by his side.
09 of 13
Theater Kids
Quinn and Kieran Culkin in 2007Credit: Christopher Porzio/Patrick McMullan/Getty
Kieran and sister Quinn enjoyed a night out at a party for the Off-Broadway production of The Scene.
10 of 13
Sharing the Spotlight
Rory and Kieran Culkin in 2009Credit: Andrew H. Walker/Getty
Rory and Kieran worked together for the second time in the movie Lymelife, starring alongside Alec Baldwin and Emma Roberts.
11 of 13
Shoulder to Lean On
Christian and Kieran Culkin in 2009Credit: Bruce Glikas/FilmMagic
Christian, the second youngest Culkin, made a rare public appearance at the cast party for Kieran’s play The Starry Messenger.
12 of 13
Always Be His Baby Bro
Kieran and Rory Culkin in 2012Credit: Jamie McCarthy/WireImage
Kieran couldn’t be prouder of his little brother at a screening of Hick, in which Rory costars with Chloë Grace Moretz and Eddie Redmayne.
13 of 13
Special Occasion
Quinn, Rory and Macaulay Culkin in 2023Credit: Amy Sussman/Getty
In a rare public outing, Quinn and Rory supported Macaulay as he received his Hollywood Walk of Fame star.
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Source: “AOL Entertainment”
