Kieran Culkin, his girlfriend, and a fateful choice between love and fandom: “You can bounce”
These days, Kieran Culkin is the Oscar-winning star of A Real Pain, not to mention the Emmy Award-winning star of Succession. These two projects showcased his unerring ability to be hilarious, aggravating, devious, and disarmingly vulnerable all at once on screen. However, his genuinely incredible portrayal of Roman Roy in Jesse Armstrong’s HBO megahit will surely be the role he is forever best known for.
Intriguingly, around the time of his Oscar win, a narrative began circulating that Culkin was effectively playing himself in both roles. It made some sense, as the star is quirkily funny and charming in real life, with a cutting sense of humour and a propensity for saying what he feels. These traits are also present and accounted for in A Real Pain and Succession. However, it must be noted that Culkin knows what he wants out of life much more clearly than either Benji Kaplan or Roman Roy – and that life includes his enduring devotion to professional wrestling.
On January 6th, 2025, WWE premiered its first episode of Monday Night Raw on Netflix, after signing a staggering $5 billion deal with the streamer. In the front row was none other than Culkin, only a day removed from winning a Golden Globe for A Real Pain. It was far from his first appearance on WWE programming, too, as he has been attending events and meeting wrestlers backstage for years. He’s also not the only Culkin who is a die-hard wrestling fanatic: his iconic brother Macauley can give him a run for his money, and younger brother Rory has also been pictured at events.
In truth, Culkin’s fandom of America’s most colourful and exaggerated form of athletic soap opera is so deeply ingrained and such a core element of his personality that, when he was once forced to choose between it and romance, it wasn’t even a difficult decision.
On his Wrestling With Freddie podcast, Freddie Prinze Jr – another celebrity grappling superfan who actually worked as a WWE writer for a period – revealed that one of Culkin’s past girlfriends wasn’t too fond of his obsession with wrestling. She couldn’t quite understand why a grown man would still cherish his closet full of wrestling toys, amassed from childhood and into young adulthood. So, she gave him an ultimatum: them or me.
“I’m sure he still loves it, but back then, like, he was so hardcore, bro,” Prinze claimed. “He had a closet full of action figures and chose them over his girlfriend at the time. He was like, ‘I’m not getting rid of those. You can bounce.’ And she did, and he was glad! He’s a gangster, bro. I love Kieran.”
At that time in his life, Culkin wasn’t prepared to part with what his girlfriend viewed as ‘childish things.’ Perhaps she didn’t quite grasp how long he and his brothers had worshipped at the altar of these lycra-clad, baby-oiled leviathans of the squared circle, and mistakenly believed it to be an ‘either/or’ situation. Instead, she asked him to do away with a significant part of his life, and something that always bonded him and his siblings. She also may have underestimated quite how passionate he was about attending wrestling events, even as a rich and famous Hollywood star.
“He’s been kicked out of a wrestling show,” Prinze laughed. He claimed it occurred when fury overtook Culkin and he hurled a beer at the seven-foot-tall WWE superstar Paul Wight, also known as Big Show. “They made up,” Prinze insisted, but the implication was clear from this act alone. No man who gets caught up in a pre-determined show so thoroughly that he throws things at the wrestlers would ever walk away from that fandom without a fight.
