This year’s awards season has certainly captured many mesmerising moments, the magic and hope of cinema shining across TVs worldwide and offering a fragment of escapism from these dark and tumultuous times. It was Sean Baker’s film Anora that swept the board at the Oscars, having the highest number of wins: taking the awards for Best Screenplay, Best Editing, Best Director, Best Actress, and, finally, Best Motion Picture. With this superb takeover, many have viewed Anora as a picturesque Cinderella fairytale. A small independent film run by indie artists, becoming the stars of the ballroom. However, there is, no doubt, another star whose road to success is a Cinderella story in itself. His name: Kieran Culkin. An actor who has transformed his career, from being known as “the Home Alone kid’s brother” to being thrown into the spotlight, collecting what seems to be an endless mass of awards and nominations. Once the forgotten brother, now an Academy Award winner. This is his story.
During the 1990s, the name Macaulay Culkin had rapidly developed into a well-known household name. Macaulay featured in the iconic blockbuster hit Home Alone, catapulting him into Hollywood fame at the age of 10. While this gave the Culkin family attention and success, challenges came hand in hand. Kieran, Macaulay’s younger brother, was a child actor himself, who also appeared in Home Alone in a minor role. Sadly, however, Macaulay’s extreme success more than overshadowed the young Kieran’s talent. For many years Kieran was recognised among the media and public as little more than “Macaulay's brother”. No one cared or even paid attention to his own acting abilities, the sole focus being on the life of his older brother. Unfortunately, this is the disappointing reflection of how the media and even the film industry can have the wrong priorities. Instead of seeking out truly talented actors, the interest can be on how much attention and drama an actor can attract to help in promotion and give “reality TV–like” gossip for magazines.
However, the tide began to change for “Macaulay’s brother” when in 2002 he bagged what could be viewed as a breakthrough role, in the film Igby Goes Down. The performance resulted in Kieran earning a Golden Globe nomination, thereby cementing him in the media as a capable actor. Though he was gaining notability, Kieran’s career still had a way to go before capturing the validation he truly deserves. The shadow of Home Alone still loomed over his career.
After taking a break from acting due to personal reasons, Kieran returned to cinema years later when the journey of his career continued to develop. His role playing Wallace Wells in Scott Pilgrim vs. the World gave a significant boost to his notability, with his portrayal of the character being loved by audiences and critics alike. While this role did not earn him any nominations or even showcase many of his technical skills, it gained him recognition among teen audiences, raising his popularity among younger people—even making him somewhat of a 2000s “heartthrob”.
Kieran’s story has already seen a journey of highs and lows, a tale of an actor fighting for his rightful place on the screen among the greats. However, the pinnacle of his career was yet to come. The prime turning point for Kieran would finally arrive in 2018—and no, it wasn’t a blockbuster film featured in cinemas worldwide. In fact, it was an HBO series that today is widely viewed as one of the greatest series ever written: Succession. Kieran starred as one of the series’ leading characters, playing the role of Roman Roy from 2018 to 2023. Starring as a character in an ongoing series can often be quite detrimental to an actor’s career, especially a rising star. This is due to audience associations and consequent typecasting into a narrow range of roles. However, I would argue that a hit series was exactly what Kieran needed to boost his career to new heights. Rather than being in a hit film every now and then with people often forgetting him, Kieran’s appearance became a constant on screen, becoming more recognisable to audiences with each episode. The series quickly became a triumph, along with Kieran’s reputation. Obviously, with this new rise of stardom, along came the awards. His performance as Roman Roy earned him a multitude of Golden Globe and Emmy nominations, with him taking home the Primetime Emmy Award for Outstanding Lead Actor in a Drama Series in 2024. Finally, he was a successful actor in his own right. Not “Macaulay’s brother” any longer. “Oh, he has a famous brother.” He was, at last, Kieran Culkin, the talented and established actor.
If you did not tune into the 97th Oscar Awards on ITV, then you may be thinking: What more can Kieran do? He’s surely peaked, reaching the pinnacle of his career. Well, I’m here to inform you otherwise. It was the magnificently talented Jesse Eisenberg who saw the even greater potential Kieran Culkin held as an actor, describing him as having an “essence”. Eisenberg cast Kieran in his 2024 comedy-drama A Real Pain. In this masterclass of a film, Kieran stars as Benji Kaplan, the cousin of Eisenberg’s character David Kaplan. In the film, the characters reunite to travel together on a Jewish heritage tour through Poland as a way of re-connecting with their past, each other, and their late grandmother. It is an understatement to say Kieran Culkin shone through the screen. He not only acted as Benji, but embodied his very soul and being, giving a heart-warming, frustrating, and deeply moving performance. In the role, he truly captured the realities of a person suffering from depression. I have never seen such a raw and authentic portrayal of this condition before and I am evidently not alone in my views. Kieran received many accolades and successful nominations for his performance, winning a number of prestigious awards, including The Golden Globe Award for Best Supporting Actor in a Motion Picture 2025, the BAFTA Award for Best Supporting Actor 2025, and the SAG Award for Outstanding Performance by a Male Actor in a Supporting role. Which is to say, he won all eight awards he was nominated for.
Finally, we reach the crown jewel—the award every actor dreams of and works for—to become an Academy Award winner, take home an Oscar, and become a part of history. On the 3rd of March 2025, Kieran Culkin’s name was announced as the 97th Academy Award winner for Best Supporting Actor in A Real Pain. He had done it—though, even with extreme success, he remained humble, making the majority of his speech about his love for his wife and children. Kieran had even tried to get out of filming A Real Pain, as he didn’t want to be away from his children.
The name Kieran Culkin should be an inspiration to us all. He has proved that you can overcome stereotypical associations and reach the highest possible success while still having the right priorities. Throughout his career, Kieran has worked hard to get his talent recognised while remembering to put his family first—and look how he has been rewarded. His life and career have truly seen a miraculous journey, from the overlooked “Macaulay’s brother” to a celebrated actor and Academy Award winner. His acting in Succession drove me to hysterical laughter, while his performance in A Real Pain brought me to tears. I cannot wait to see where Kieran goes from here. If writers, producers, and directors have any sense, they will snap him up—and I will be the first in the cinema to enjoy the film.