Hollywood’s most dazzling week of the year wrapped up in true star-studded fashion, as the 2026 Oscars and their surrounding festivities unfolded with all the spectacle and surprises fans have come to expect. Yet, while the red carpets, exclusive parties, and after-hours celebrations dominated Los Angeles, one of the night’s biggest headlines was the notable absence of Sean Penn, who chose a different stage for his moment in the spotlight—Kyiv, Ukraine.
Let’s start at the Dolby Theatre, where the Oscars ceremony on March 16, 2026, crowned its latest set of winners. Among them was Sean Penn, who clinched his third Academy Award for Best Supporting Actor for his role in One Battle After Another. With this win, Penn joined an elite club of actors—Daniel Day-Lewis, Jack Nicholson, and Walter Brennan—each boasting three acting Oscars. But when Kieran Culkin, last year’s winner for A Real Pain, opened the envelope and called Penn’s name, the audience was met with a surprise. "Sean Penn couldn't be here this evening – or didn't want to – so I'll be accepting the award on his behalf," Culkin quipped, leaving viewers puzzled about Penn’s whereabouts, according to The Hollywood Reporter.
The mystery was soon solved. As AFP reported, Penn was thousands of miles away in Kyiv, Ukraine, meeting with President Volodymyr Zelenskyy. A senior Ukrainian official explained, "We can say that he's in Ukraine, but it's his personal visit; that's how he sees it, that he needs to be in Ukraine. He just wants to support Ukraine." Zelenskyy himself took to social media to thank the actor, writing, "Sean, thanks to you, we know what a true friend of Ukraine is. You have stood with Ukraine since the first day of the full-scale war. This is still true today. And we know that you will continue to stand with our country and our people.”
Penn’s commitment to Ukraine is not new. Since Russia’s invasion in 2022, he has made multiple trips to the country, documenting its struggle and resilience. In 2022, Penn famously described Ukraine’s defense as “the tip of the spear for the democratic embrace of dreams,” warning that “if we allow it to fight alone, our soul as America is lost.” That same year, in a symbolic gesture, he presented one of his Oscars to Zelenskyy, promising to leave it in Kyiv until Ukraine’s victory. For his unwavering support, Ukraine awarded Penn the Order of Merit, third degree. His documentary Superpower, chronicling the war and Zelenskyy’s leadership, premiered at the Berlinale in 2023, earning widespread attention.
Back in Los Angeles, Oscar week was nothing short of a whirlwind. The days leading up to the ceremony were packed with exclusive dinners, glittering galas, and industry gatherings. On March 14, the Chanel and Charles Finch Pre-Oscar Dinner drew nominees and A-listers alike, with stars such as Nicole Kidman, Lily-Rose Depp, Kristen Stewart, and Teyana Taylor mingling at the Polo Lounge. Taylor, nominated for her supporting role in One Battle After Another, admitted she was “so nervous” for the big night, planning to be one of the first on the carpet and hoping a passionfruit margarita would help calm her nerves.
That same weekend, Giorgio Armani opened its Rodeo Drive store for a chic cocktail event, attracting stars from across entertainment and fashion, while the Motion Picture Television Fund’s Night Before benefit raised over $4 million to support industry professionals in need. Kate Hudson, Michael B. Jordan, Anne Hathaway, and Christopher Nolan were among those lending their support, with Diplo spinning a DJ set and Brittany Howard performing a track from the Oscar-winning film Sinners.
When the curtain finally fell on the Oscars ceremony, the celebrations only intensified. Vanity Fair’s legendary afterparty, relocated this year to the Los Angeles County Museum of Art (LACMA), was a who’s-who of Hollywood royalty. The festivities began with an intimate dinner for about 100 guests, before a crush of revelers arrived to pose in front of a striking 100-foot-long silver wall, flanked by illuminated Rodin sculptures. According to Vanity Fair, the guest list was a testament to the industry’s diversity and star power—Michael B. Jordan, Jessie Buckley, Regina Hall, Teyana Taylor, and others from the Best Picture winner One Battle After Another mingled with the likes of Timothée Chalamet, Kylie Jenner, Emma Stone, Nicole Kidman, Robert Pattinson, and even Steven Spielberg and Mick Jagger. To preserve the party’s mystique, social media was discouraged, with stickers handed out to cover camera phones.
Meanwhile, Madonna and Guy Oseary’s ultra-exclusive late-night afterparty, simply dubbed “The Party,” continued its tradition of secrecy—no photography, no social posts, just A-listers letting loose. Taylor Swift, Travis Kelce, Justin and Hailey Bieber, and Kim Kardashian were just a few of the stars who stopped by, with guests leaving clutching Gucci-branded party favors and T-shirts cheekily labeled “Stolen From GuyO’s House.”
Philanthropy was also front and center during Oscar week. Elton John’s annual Academy Awards Viewing Party in West Hollywood raised a staggering $10.6 million for the Elton John AIDS Foundation. As John joked to the crowd, “Throughout the years we’ve raised a lot of money, I think $125 million since we started. Which has gone towards my wardrobe that I wear tonight.” The event featured a spirited auction—dinner with John and David Furnish, plus a private performance, fetched $900,000—and a rousing set by Grammy winner Lola Young. “Elton, David and the Foundation are all about celebrating who you really are, and that’s exactly what my music is about,” Young said, emphasizing the ongoing fight for HIV prevention and LGBTQ+ rights.
Netflix, not to be outdone, threw its own afterparty at The Living Room, with executives Ted Sarandos and Dan Lin joining the teams behind its nominated films. The Governors Ball, the Academy’s official post-Oscars bash, saw winners getting their golden statuettes engraved, with culinary legend Wolfgang Puck providing the menu for the 32nd consecutive year.
Of course, the Oscars wouldn’t be the Oscars without a nod to fashion. Designer Philipp Plein’s annual runway show in Bel Air saw models arriving in custom Rolls Royces, dazzling crowds with gold, silver, and black beaded mini-dresses. Diane von Furstenberg’s luncheon for female nominees, now in its thirteenth year, celebrated the achievements of women behind the scenes, with the designer urging guests to “make connection and remember to be a badass, and kind.”
As the formalwear is tucked away and the last of the party favors are pocketed, Oscar week 2026 will be remembered not only for its glitz and glamour, but for moments of genuine solidarity and purpose. Whether it was Sean Penn standing with Ukraine or Elton John rallying support for HIV/AIDS causes, the week proved that Hollywood’s biggest night is about more than just awards—it’s about using the spotlight to make a difference.