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Conan O'Brien Imagines Oscar Win Serenaded by Josh Groban in Dream Sketch
Instagram/Conan O'Brien & Josh Grob
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Conan O'Brien hosts the 2026 Oscars with a hilarious fantasy of winning an Oscar himself, poking fun at awards show humility in classic comedic style.

AceShowbiz - Conan O'Brien brought humor and whimsy to the 98th Annual Oscars ceremony on March 15, 2026, held at the Dolby Theatre in Hollywood, California. As the night’s host, he delivered a memorable segment imagining himself as an Oscar winner, showcasing his characteristic wit and playful style.

During the broadcast, Conan O'Brien reflected on the typical humility shown by Oscar recipients, noting how winners often thank their teams and spouses. He commented, "It's refreshing to see all this modesty and genuine humility," but then admitted he might react differently if he ever won, setting the stage for a comedic dream sequence.

In this fantasy scenario, O'Brien was nominated for a fictional "Best Achievement Oscar," competing against well-known Academy favorites such as Antonio Banderas, Renee Zellweger, Denzel Washington, and Glenn Close. When the winner was announced, the former late-night host stood triumphant, wearing a velvet robe and crown while receiving blessings from a cardinal, embracing his victory in grand fashion.

Adding to the spectacle, Josh Groban appeared on stage to serenade O'Brien with a song celebrating his mock triumph. The lyrics humorously declared, "His Oscar win has been fated by God / He did this himself, and he's grateful to none / Even the haters can't hate number one." This musical moment highlighted the playful nature of the segment.

The comedic bit continued with O'Brien summoning a falcon named Cicero to deliver his Oscar statuette from the sky, jokingly promising the audience, "This is how all Oscars will be handed out tonight." This imaginative touch added to the night’s lighthearted tone.

This marked Conan O'Brien’s second consecutive year hosting the Academy Awards, following his debut as Oscars host the previous year. Beyond the Oscars, he has also hosted the Emmys twice, in 2002 and 2006, underscoring his extensive experience as an awards show emcee.

The 2026 Oscars ceremony featured a blend of humor and celebration, with O'Brien’s playful dream sequence standing out as a highlight that entertained viewers while paying homage to the grandeur of the event.

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