Oscars 2026 Biggest Moments

The 98th Academy Awards delivered everything audiences expect from Hollywood’s biggest night: historic wins, emotional speeches, viral jokes, and unforgettable pop-culture crossovers. Hosted by Conan O’Brien, the ceremony blended sharp humor with heartfelt tributes and groundbreaking milestones.

From a playful roast of Timothée Chalamet to a surreal on-stage encounter between Anna Wintour and Anne Hathawaythat felt ripped straight out of The Devil Wears Prada, here are the biggest moments that defined the 2026 Oscars.

A Big Night for One Battle After Another

The night’s biggest winner was the political epic One Battle After Another, directed by Paul Thomas Anderson. The film dominated the ceremony, taking home six Oscars, including Best Picture, Best Director, and Best Adapted Screenplay.

During his acceptance speech, Anderson reflected on the film’s themes of political turmoil and generational responsibility, describing the project as an “apology” to his children for the chaotic state of the world.

The film’s sweeping victory marked a long-awaited milestone for Anderson, who had previously been nominated multiple times but had never won an Oscar.

Conan O’Brien’s Opening Monologue Sets the Tone

Returning as host, Conan O’Brien opened the show with a monologue packed with pop-culture references, political commentary, and Hollywood inside jokes. His comedic style kept the ceremony lively and balanced the night’s more serious moments.

One of the biggest laughs came when O’Brien playfully roasted Timothée Chalamet a frequent awards-season nominee, poking fun at his artistic persona and high-profile roles. The gag quickly circulated on social media as one of the evening’s most talked-about comedic highlights.

The Real-Life Devil Wears Prada Moment

One of the night’s most viral moments came when fashion power player Anna Wintour appeared on stage alongside Anne Hathaway to present awards.

Fans of The Devil Wears Prada instantly recognized the meta joke. In the 2006 film, Hathaway plays Andy Sachs, the assistant to the intimidating editor Miranda Priestly a character widely believed to be inspired by Wintour.

During their presentation, Hathaway asked Wintour what she thought of her dress.

Wintour replied with a deadpan pause before moving on to the nominees.

Then came the punchline:
Wintour jokingly addressed Hathaway as “Emily,” referencing the character played by Emily Blunt in the original film.

The exchange instantly became one of the ceremony’s most shared clips online and a clever bit of promotion for the upcoming sequel to the beloved fashion comedy.

Historic Wins for Sinners

The gothic vampire drama Sinners, directed by Ryan Coogler, also had a strong showing.

The film earned four Oscars, including Best Actor for Michael B. Jordan.

Another historic milestone came when cinematographer Autumn Durald Arkapaw became the first woman and first woman of color to win the Oscar for Best Cinematography.

Her win marked a significant moment for representation behind the camera.

Jessie Buckley’s Emotional Best Actress Victory

Best Actress went to Jessie Buckley for her role in Hamnet.

Buckley’s win capped a remarkable awards-season sweep that included BAFTA, Golden Globe, SAG, and Critics Choice victories.

In an emotional speech, Buckley dedicated the award to her infant daughter and celebrated the creativity and resilience of women across generations.

Amy Madigan’s Long-Awaited Oscar Moment

Another emotional highlight came when veteran actress Amy Madigan won Best Supporting Actress for her performance in Weapons.

Madigan, 75, earned the award more than 40 years after her first Oscar nomination, making her victory one of the most inspiring moments of the evening.

During her speech, she thanked her family and credited her husband, actor Ed Harris, for supporting her throughout her career.

Nostalgia and Tributes

The ceremony also delivered emotional tributes and nostalgic reunions.

A special segment honored legendary figures who passed away during the year, with heartfelt tributes delivered by Hollywood icons including Billy Crystal and Barbra Streisand.

Meanwhile, the cast of Bridesmaids reunited on stage to present an award, celebrating the film’s anniversary and bringing a dose of comedy nostalgia to the show.

The Bigger Message of the Night

Beyond the glamour and humor, the 2026 Oscars reflected a film industry grappling with change from political themes in major films to conversations about artificial intelligence and the future of filmmaking.

Despite those shifts, the night reinforced a familiar truth: cinema’s power lies in storytelling and human creativity.

As the curtain closed on the 98th Academy Awards, Hollywood once again proved that its biggest stage is about more than awards, it’s about moments that capture culture in real time.