Why Macaulay Culkin “Cried” Over Brother Kieran Culkin’s Oscar Win

Oscars 2025: Kieran Culkin Makes Another Pregnancy Pact With Jazz Charton After Win

Kieran Culkin isn’t celebrating alone.

The A Real Pain star, who won the Oscar for Best Supporting Actor during the March 2 ceremony, was being cheered on by his brother Macaulay Culkin, who shared his emotional reaction to Kieran’s win.

“I cried,” Macaulay told Tan France on the red carpet of the Vanity Fair after party March 2. “He’s Academy Award-winning actor Kieran Culkin.”

The Home Alone star, who stood alongside fiancée Brenda Song, texted his brother immediately after the win: “I was like, ‘I’m gonna see you later.’”

And as if the bond with his brother wasn’t already proven by his emotional reaction, Macaulay confessed that Kieran had his full attention during the awards show.

“Just the Best Supporting Actor,” Macaulay noted, “that’s the only thing I watched. True story, true story.”

While the 44-year-old was sure to tune into the broadcast, he didn’t have any doubt that his brother would take home Oscar gold.

“He was front row, aisle, closest to the stairs,” he explained. “There was no way he was not going to win.”

But Macaulay wasn’t the only family member cheering Kieran on to victory. Brenda—who shares sons Dakota, 3, and Carson, 2, with Macaulay—was just as confident in the Succession alum’s chances, commenting, “Let’s be real. We’re allowed to say that.”

And though Brenda was rooting for Kieran during Hollywood’s biggest night, it wasn’t the first time she has been vocal with her support for him.

Jeff Kravitz/FilmMagic

“He’s such a brilliant actor,” she told E! News Feb. 13. “How can you not be proud? I’m so happy for him.”

She also revealed that though Kieran—who won the Golden Globe, SAG Award, Critics Choice Award and BAFTA Film Award in the lead up to the Oscars—is often sarcastic in his acceptance speeches, he shares in the pride of his work.

“All of his awards are displayed,” she continued. “That’s the thing about it, it’s all in jest. He has such an incredible sense of humor and it’s also self-deprecating humor and it’s wonderful.”

She added, “At the end of the day, this is a job. This is crazy that we get to do this and that’s why he handles it the way he does, which is brilliant.”

Read on to see who else took home trophies during the 2025 Oscars.

Best Picture

WINNER: Anora

The Brutalist

A Complete Unknown 

Conclave

Dune: Part Two

Emilia Pérez 

I’m Still Here

Nickel Boys 

The Substance

Wicked

Best Actress in a Leading Role

Cynthia Erivo – Wicked

Karla Sofía Gascón – Emilia Pérez 

WINNER: Mikey Madison – Anora

Demi Moore – The Substance

Fernanda Torres – I’m Still Here

Best Actress in a Supporting Role

Monica Barbaro – A Complete Unknown 

Ariana Grande – Wicked 

Felicity Jones – The Brutalist

Isabella Rossellini – Conclave

WINNER: Zoé Saldaña – Emilia Pérez

Best Actor in a Leading Role

WINNER: Adrien Brody – The Brutalist

Timothée Chalamet – A Complete Unknown 

Colman Domingo – Sing Sing

Ralph Fiennes – Conclave

Sebastian Stan – The Apprentice

Best Actor in a Supporting Role

Yura Borisov – Anora

WINNER: Kieran Culkin – A Real Pain 

Edward Norton – A Complete Unknown 

Guy Pearce – The Brutalist

Jeremy Strong – The Apprentice

Best Directing

WINNER: Sean Baker – Anora

Brady Corbet – The Brutalist

James Mangold – A Complete Unknown  

Jacques Audiard – Emilia Pérez

Coralie Fargeat – The Substance

Best Makeup and Hairstyling

Mike Marino, Dave Presto and Crystal Jurado – A Different Man

Julia Floch Carbonel & Simon Livet – Emilia Pérez

Traci Loader, Suzanne Stokes-Munton & David White – Nosferatu 

WINNER: Pierre-Olivier Persin – The Substance

Frances Hannon, Sarah Nuth, Laura Blount – Wicked

Best Live Action Short

A Lien 

WINNER: I’m Not a Robot

Anuja 

The Last Ranger

The Man Who Could Not Remain Silent

Best International Feature Film

WINNER: I’m Still Here

The Girl with the Needle 

Emilia Pérez

The Seed of the Sacred Fig

Flow

Best Film Editing

WINNER: Anora

The Brutalist

Conclave

Emilia Pérez

Wicked

Best Costume Design

Arianne Phillips – A Complete Unknown

Lisy Christy – Conclave

Janty Yates – Gladiator II 

Linda Muir – Nosferatu

WINNER: Paul Tazewell – Wicked

Best Original Screenplay

WINNER: Sean Baker – Anora 

Brady Corbet & Mona Fastvold – The Brutalist 

Jesse Eisenberg – A Real Pain

Tim Fehlbaum & Moritz Binder – September 5 

Coralie Fargeat – The Substance

Best Adapted Screenplay

Jay Cocks & James Mangold – A Complete Unknown 

WINNER: Peter Straughan – Conclave

Jacques Audiard, Thomas Bidegain, Nicolas Livecchi – Emilia Pérez

Joslyn Barnes & RaMell Ross – Nickel Boys

Clint Bentley & Greg Kwedar – Sing Sing 

Best Visual Effects

Alien: Romulus 

Better Man

WINNER: Dune: Part Two

Kingdom of the Planet of the Apes

Wicked

Best Sound

A Complete Unknown

WINNER: Dune: Part Two

Emilia Pérez

Wicked

The Wild Robot

Best Production Design

Judy Becker – The Brutalist

Suzie Davies & Roberta Federico – Conclave

Zsuzsanna Sipos, Shane Vieau & Patrice Vermette – Dune: Part Two 

Beatrice Brentnerova, Paul Ghirardani & Craig Lanthorp – Nosferatu

WINNER: Nathan Crawley – Wicked

Best Original Song

WINNER: “El Mal” written by Clement Ducol, Camille & Jacques Audiard, performed by Zoé Saldaña and Karla Sofía Gascon – Emilia Pérez

“The Journey” written by Diane Warren, performed by H.E.R. – The Six Triple Eight

“Like a Bird” written by Adrian Quesada and Abraham Alexander-  Sing Sing

“Mi Camino” written by Clement Ducol & Camille, performed by Selena Gomez & Edgar Ramirez – Emilia Pérez

“Never Too Late” written by written by Elton John, Brandi Carlile, Bernie Taupin, and Andrew Watt, performed by Elton John – Elton John: Never Too Late

Best Original Score

WINNER: The Brutalist

Conclave

Emilia Pérez

Wicked

The Wild Robot

Best Cinematography

WINNER: Lol Crawley – The Brutalist

Greig Fraser – Dune: Part Two

Paul Guilhaume – Emilia Pérez

Edward Lachman – Maria

Jarin Blaschke – Nosferatu

Best Animated Feature Film

WINNER: Flow

Inside Out 2

Memoir of a Snail 

Wallace & Gromit: Vengeance Most Fowl

The Wild Robot

Best Animated Short Film

Beautiful Men

WINNER: In the Shadow of the Cypress

Magic Candies

Wander to Wonder

Yuck!

Best Documentary Feature Film

Black Box Diaries

WINNER: No Other Land 

Porcelain War

Soundtrack to a Coup d’Etat

Sugarcane

Best Documentary Short Film

I Am Ready, Warden

Death By Numbers

Incident 

Instruments of a Beating Heart 

WINNER: The Only Girl in the Orchestra

For the latest breaking news updates, click here to download the E! News App