Macaulay Culkin Celebrates Brother Kieran's Oscar Win with Brenda Song at Vanity Fair Party

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Macaulay Culkin put on a very animated display as he celebrated brother Kieran's Oscar win with girlfriend Brenda Song at Vanity Fair's after-party in Hollywood on Sunday evening. The Home Alone star, 44, was in great spirits after his younger sibling, 42, walked away with the Best Supporting Actor gong for A Real Pain. Macaulay whipped off his loafers and frolicked with stunning girlfriend Brenda Strong, 36, inside the VIP event which took place at the Wallis Annenberg Center.

The former child star looked dapper in his suit and posed up a storm on the red carpet before deciding to take off his shoes and walk around in socks. Meanwhile Brenda stunned in a strapless white pleated gown which boasted a dramatic train and was accessorised with dazzling diamond earrings. The couple, who share two sons, appeared as they cosied up together and partied the night away to celebrate Kieran's triumph. The Oscars ceremony saw a number of surprise wins, including Mikey Madison beating Demi Moore to the Best Actress award for her role in Anora.

Demi Moore was left crushed as Mikey Madison beat her to the coveted Best Actress award at the 2025 Oscars, on a night when Anora dominated with five wins including Best Picture. Other big winners on Sunday night included Zoe Saldana, who took home the Best Supporting Actress award for her role in the controversial Emilia Perez, and Adrien Brody, who triumphed over Timothée Chalamet for the Best Actor award with his performance in The Brutalist. Kieran kicked off the evening with a Best Supporting Actor win for A Real Pain. The winners of the night included:

  • Best Picture: Anora
  • Actress in a Leading Role: Mikey Madison — Anora
  • Actor in a Leading Role: Adrien Brody — The Brutalist
  • Actress in a Supporting Role: Zoe Saldaña — Emilia Pérez
  • Actor in a Supporting Role: Kieran Culkin — A Real Pain
The film Anora also earned the Best Director award for Sean Baker, as well as the Original Screenplay award.

Macaulay Culkin and Brenda Song's appearance at the Vanity Fair Oscar Party was just one of many celebrity sightings at the event, which was attended by over 300 stars. The party took place at the Wallis Annenberg Center for the Performing Arts in Beverly Hills, and featured a number of other winners and nominees from the Oscars ceremony. Brenda Song wore a Marmar Halim cream silk taffeta fan pleated draped strapless gown with a train from the brand’s Fall-Winter 2025 Bridal Collection. Macaulay Culkin held onto his wife as he interlocked his fingers with his arms around her, and the couple posed for photos together on the red carpet.

The Oscars ceremony was marked by a number of surprise wins and memorable moments, including Demi Moore's reaction to losing the Best Actress award to Mikey Madison. According to a lip reader, Demi Moore's one-word response to losing the award was "nice". The ceremony also featured a number of performances and tributes, and was attended by a wide range of celebrities from the film industry. The film industry was out in full force to celebrate the best in cinema, and the Vanity Fair Oscar Party was the perfect place to see all the stars in one place.

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