There is no night in Hollywood quite like the Oscars, filled with dazzling red carpet appearances, heartfelt acceptance speeches, and unexpected reunions. Of course, there are many award nights, as Moira Rose (Catherine O’Hara) from Schitt’s Creek once described award season as her favorite. However, the Academy Awards always bring a special charm to close out the season, and this year was no exception. The 2025 Oscars, hosted by Conan O’Brien, delivered a mix of memorable moments—some spectacular and others puzzling. Here’s a roundup of the highlights and lowlights from this year’s ceremony.
One of the most breathtaking moments of the night was the opening performance featuring Cynthia Erivo and Ariana Grande. It felt like a dream come true when Grande, wearing a ruby-red dress reminiscent of Dorothy’s slippers, took the stage to sing Somewhere Over the Rainbow. Just when it seemed things couldn’t get better, Erivo followed with a stirring rendition of Home. The magic continued as the Wicked co-stars joined hands for the climactic portion of Defying Gravity, where Glinda steps aside, allowing Elphaba to take center stage. Their flawless harmonization and emotional delivery set the perfect tone for the night.
Adam Sandler, known for his comedic brilliance and casual wardrobe choices, combined both for a hilarious moment during Conan O’Brien’s opening monologue. Seated in the audience, Sandler appeared in his signature basketball shorts and hoodie, prompting O’Brien to joke, “You’re dressed like a guy playing video poker at 2 a.m.” Feigning offense, Sandler stormed out of the Dolby Theatre but not before inviting everyone to join him for a game of five-on-five basketball. He even took a moment to shout a playful “Chalameeeetttt!” at Timothée Chalamet before making his grand exit.
Kieran Culkin not only won an Oscar but also reignited a personal bet with his wife, Jazz Charton. Accepting the award for Best Supporting Actor for A Real Pain, Culkin recalled a past awards show where he publicly mentioned wanting a third child because his wife had jokingly agreed—never expecting him to win. He then revealed that after his Emmy win for Succession, he told his wife he actually wanted four kids. Her response? “I will give you four when you win an Oscar.” Seizing the moment, Culkin looked into the camera and addressed his wife directly: “Love of my life, ye of little faith, no pressure, I love you, I’m really sorry I did this again, and let’s get cracking on those kids. What do you say?”
Not every moment of the ceremony was well-received, particularly the perplexing James Bond tribute. While celebrating the legendary franchise seemed fitting, especially with the Broccoli family recently handing creative control to Amazon MGM, the execution left many confused. The tribute began with a traditional video montage, but things took a strange turn when Margaret Qualley took the stage to perform a dance routine. This was followed by performances from Blackpink’s Lisa, Doja Cat, and Raye, who sang three different Bond theme songs. The most baffling aspect was that this elaborate segment took place on a night when performances of the Best Original Song nominees had been cut. The result was a confusing spectacle that left audiences wondering: why?
The Oscars also found a creative way to honor the heroic members of the Los Angeles Fire Department. O’Brien welcomed LAFD firefighters onstage, prompting a standing ovation. However, instead of stopping there, he had them participate in a comedic bit where they read jokes from the teleprompter—lines that O’Brien himself wasn’t daring enough to deliver. One of the standout jokes: “Our hearts go out to all of those who have lost their homes — and I’m talking about the producers of Joker 2.” The firefighters embraced the humor, making for a lighthearted and memorable segment.
Unfortunately, technical difficulties put a damper on the evening for some viewers when Hulu experienced a major outage. Given the enormous viewership expected for the Oscars, streaming issues were the last thing anyone wanted. Early in the show, many users found themselves unable to watch, and according to DownDetector.com, more than 30,000 people were affected. The frustration peaked at the end of the ceremony when the livestream abruptly cut off during Sean Baker’s Best Director acceptance speech, with two major categories still left to be announced. The abrupt outage raised questions about whether Hulu had underestimated the show’s runtime.
June Squibb proved once again why she is a Hollywood treasure. At 95 years old, Squibb was simply presenting an award, yet she managed to steal the spotlight. Standing alongside Scarlett Johansson, Squibb playfully joked about the power of Hollywood makeup artists. “I’m actually being played by Bill Skarsgård right now,” she quipped. “Half the time you see me in public, it’s Bill Skarsgård. The real June Squibb is at home with a book right now.” While the bit was a hit, there was a disappointing lack of a standing ovation for the legendary actress. Given her immense contributions to cinema, her presence alone should have prompted the entire room to rise in applause.
The night also included an emotional tribute to the late Gene Hackman, a two-time Oscar-winning legend whose passing deeply affected Hollywood. To honor him, the Academy invited Morgan Freeman, who co-starred with Hackman in Unforgiven and Under Suspicion, to introduce the In Memoriam segment. Freeman shared a heartfelt message, quoting Hackman: “Gene always said, ‘I don’t think about legacy, I just hope people remember me as someone who tried to do good work.'” He then added, “So I think I speak for us all when I say, Gene, you’ll be remembered for that and for so much more. Rest in peace, my friend.”
The 2025 Oscars delivered a mix of breathtaking performances, heartfelt speeches, and a few perplexing missteps. From Ariana Grande and Cynthia Erivo’s show-stopping opening to Kieran Culkin’s playful family planning announcement, the night was filled with unforgettable moments. However, the James Bond tribute left audiences scratching their heads, and Hulu’s untimely outage frustrated many viewers. Despite a few stumbles, the Academy Awards once again proved why they remain the pinnacle of Hollywood’s award season.