Oscars 2025: Best and Worst Moments

Wicked besties Cynthia Erivo and Ariana Grande got the Oscars off to a soaring start Sunday night with a musical medley that brought the audience on a journey through the extended Wizard of Oz universe. Grande emerged first, offering up a soulful rendition of the timeless classic “Somewhere Over the Rainbow,” before Erivo joined her to pay homage to The Wiz, singing “Home,” performed by Diana Ross in the 1978 film. The pair then segued into their inevitable duet, “Defying Gravity,” the climax of Wicked (or Part One, anyway), with Erivo taking figurative flight for a chills-worthy finale. It’s odd for just one Best Picture nominee to get all that prime real estate at the start of the show, but nobody seemed to mind the victory lap for 2024’s blockbuster musical, especially when the singers have pipes like these. —Miles Klee

It was a truly WTF year in terms of the lead-up to Oscars — so why not officially kick the show off with something that matched the delirium, the lunacy, and the sheer unpredictability of the post-nomination campaigning? The Academy likely thought it was hiring the Conan O’Brien who had years of talk-show hosting under his belt and did a very professional job emceeing the Emmys (twice). The guy who showed up on the Dolby Theater’s stage, however, was closer to the chaos agent responsible for the early Late Night years and the “Monorail” episode of The Simpsons. O’Brien did an entire throw-to-the-audience bit with Adam Sandler; teased Timothée Chalamet about his bright yellow suit (“You won’t get hit on your bike tonight”) and his age (showing what he purported to be an old Lil’ Timmy headshot but was a picture of a sonogram); and ended with an elaborate musical number about not wasting people’s time that featured a Dune sandworm playing “Chopsticks” on a piano. He even addressed the scandal surrounding Karla Sofía Gascón’s tweets in a way that was sharp but not mean. It was absurd, it was funny, it set the perfect anything-goes tone from the jump. It was vintage Conan. —David Fear

Culkin winning Best Supporting Actor for his role in A Real Pain was one of the few sure things going into the Academy Awards. And given the goofy, off-the-cuff (and often profane) speeches he’d been giving as he collected a slew of statues leading up to the Oscars, it was an equally foregone conclusion that his thanks from the podium would be memorable. After being muted for close to 10 seconds when he gave a potty-mouthed shoutout to his former Succession co-star and fellow nominee Jeremy Strong, Culkin sped through a few quick thank yous before directly addressing his wife. Back when he won an Emmy in 2023, the actor joked from the stage about wanting a third child and mentioned that his wife promised to deliver if he won. In this speech, he revealed that when he’d later joked that he wanted a fourth, Mrs. “Ye of Little Faith” said that she’d consider another kid if he ever won an Oscar. He then held up his statue as the crowd — and thankfully, his wife — cracked up. —D.F.

Everyone watches the Academy Awards for the big-name actors, so it’s not uncommon for behind-the-scenes nominees to get minimal camera time and vague descriptions of what they actually do. So it was a welcome surprise to see five stars of the films up for best costume design — Conclave, Gladiator II, A Complete Unknown, Wicked, and Nosferatu — give personal and heartfelt appreciations to their costumers. Alas, only Bowen Yang was committed enough to wear his onscreen threads, a whimsical school uniform from Wicked, and he felt quite betrayed by his co-presenters, especially supposed “bestie” John Lithgow. But it was the musical fantasy that triumphed thanks to the work of Paul Tazewell, who is now three-fourths of the way to an EGOT, having previously won a Tony and an Emmy. He began his speech by noting that he was the first Black man to claim an Oscar for costume design, which brought many in the audience to their feet with applause, among them Elphaba herself, Cynthia Erivo. —M.K.

Those of you who wondered, “Is that Ron Swanson announcing the show?” early on the night were vindicated when host Conan O’Brien got into a brief argument with the voice of god — indeed supplied by none other than Nick Offerman. As O’Brien attempted to launch into an Oscars history lesson, Offerman interjected in whiskey-smooth tones to observe that it was the comedian’s first time hosting the Academy Awards. He proceeded to get into O’Brien’s head about the “pressure” he was under to perform at the top of his game, at one point musing: “A challenge this big coming so late in one’s career must weigh on a man’s soul.” An exasperated O’Brien finally told Offerman to quit interrupting and read the script he’d supplied. Offerman waited just a beat before blandly reading that O’Brien “is one of the great comedians of our time,” to the host’s apparent satisfaction. It’s not often that you get to see the accepted conventions of a televised award show turned upside-down; maybe other ceremonies should try shaking it up once in a while? —M.K.

Back in November, longtime producers of the James Bond movies — Michael G. Wilson and Barbara Broccoli — were honored at the Academy’s Governor’s Awards, receiving the prestigious Irving Thalberg Memorial Award. So the decision to pay tribute to them at the Oscars had probably been in the works long before it was announced that Amazon had taken control of a franchise that had essentially been run like a family business for six decades. It would have been a not-great idea to honor these legends with a stage full of interpretive dancers (including Margaret Qualley?) and singers like Blackpink’s Lisa, Doja Cat, and Raye covering famous Bond-film themes, even if the lingering odor of this corporate takeover wasn’t still wafting in the air. To be fair, Raye’s cover of the opening song from Skyfall was sublime. But dear god, this was one Rob Lowe and Snow White away from the 1989 Oscars musical fiasco. —D.F.

The critically praised — yet still officially sans distribution — doc about the forced displacement of a community in the West Bank, filmed by both Palestinian and Israeli activists, had been an odds-on favorite to win the Best Documentary Oscar, though some feared that its unfiltered look at a hot-button topic was be too politically divisive to many voters. When the quartet of filmmakers took the stage to accept the award, Palestinian director Basel Adra spoke first, mentioning that he hoped his daughter would not grow up in a landscape of “ethnic cleansing.” Then one of his Israeli comrades, Yuval Abraham, stepped to the mic and pointed out that, though the film was made in the spirit of cross-cultural love and cooperation, the country he lived in was one of freedom of movement, and Adra’s one of military law. He offered that there is a path forward, and that “the foreign policy in this county is helping to block [that path]… There is another way. It’s not too late for life and the living. There is no other way.” For an evening in which politics had been a conspicuous absence (save Daryl Hannah shouting out Ukraine), the declaration felt like a much-needed nod to the world outside the theater. —D.F.

It’s not as though legendary songwriter Diane Warren is lacking for recognition: The creative force behind massive pop hits including Cher’s “If I Could Turn Back Time” and Celine Dion’s “Because You Loved Me” has won enough music-industry awards to fill a couple of display cases. But Warren has been unlucky when it comes to the Oscars, despite already earning an honorary one. She’s been nominated 16 times for Best Original Song since 1987, and every single year going back to 2017, yet she came up short once again with her latest entry, “The Journey.” Performed by Oscar-winning artist H.E.R., the anthem was featured in The Six Triple Eight, a historical drama about an all-Black, all-female battalion during World War II. Snagging the prize instead were husband-and-wife songwriters Clément Ducol and Camille for “El Mal,” sung by Zoe Saldaña in Emilia Pérez. Camille attempted to sing a bit herself during her thank-yous, to a somewhat tepid response from an audience that may have preferred to see Warren finally bring home the gold. —M.K.

And lo, a screwball comedy about a sex worker shall lead them! Sean Baker’s delirious, indie-film answer to Pretty Woman cleaned up, taking home Oscars for Best Editing, Best Original Screenplay, Best Director, Best Actress (big up Mikey Madison!), and Best Picture, thus proving that fairy tales sometimes do come true. Baker used his Best Director speech to stump for the importance of the theatrical releases, and encouraged distributors, filmmakers, and moviegoers with kids to keep the big-screen experience alive. Both he and Madison gave shoutouts to the sex-worker industry, and at the end of a round of speeches from the producers after the Best Pic win, Baker added, “Long live independent film!” It felt like an uplifting end to a surprisingly giddy night for movie lovers. —D.F.