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Oscars 2026 Unforgettable Moments: Conan O’Brien’s Rapid-Fire Jokes, Anna Wintour’s ‘Devil Wears Prada’ Tribute and Jimmy Kimmel’s Trump Dig Steal the Show

The 98th Academy Awards delivered laughter, nostalgia, and dazzling performances as Hollywood’s biggest night produced several viral moments that had audiences talking long after the curtain closed.

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Oscars 2026 Highlights: Conan O’Brien Jokes, Anna Wintour Moment and Jimmy Kimmel’s Trump Dig
Comedian Conan O’Brien delivers rapid-fire jokes during the 98th Academy Awards, one of the most talked-about moments of Oscars 2026.

Hollywood’s most glamorous evening once again delivered a mix of elegance, humor, and unexpected moments. The Academy Awards — officially the 98th Academy Awards — transformed the iconic Dolby Theatre in Los Angeles into a stage for unforgettable pop-culture highlights.

While awards and emotional speeches remain the heart of the Oscars, it’s often the unscripted moments, sharp jokes, and surprise appearances that define the night. From comedian Conan O’Brien firing off rapid-fire jokes to fashion legend Anna Wintour embracing a cinematic reference to The Devil Wears Prada, the evening unfolded like a perfectly timed Hollywood spectacle.

Here’s a closer look at some of the most memorable moments from the 2026 ceremony.


Conan O’Brien’s Rapid-Fire Comedy Had the Room Roaring

One of the evening’s most talked-about highlights came from veteran comedian and television host Conan O’Brien. Known for his quick wit and signature self-deprecating humor, O’Brien delivered a string of rapid-fire jokes that had the audience laughing throughout the broadcast.

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Hollywood events can sometimes feel overly formal, but O’Brien’s comedic timing injected a dose of unpredictability. His jokes bounced between playful Hollywood satire and cultural commentary, reminding viewers why he remains one of the entertainment industry’s most respected comic voices.

Social media quickly lit up with clips of the moment, with many viewers calling it one of the funniest Oscar appearances in recent years.


Anna Wintour Channels ‘The Devil Wears Prada’

Fashion also had its moment on stage when Anna Wintour, the influential editor-in-chief of Vogue, made a striking appearance that instantly sparked comparisons to the iconic film The Devil Wears Prada.

The reference was impossible to miss. Wintour — widely believed to have inspired the character of Miranda Priestly in the film — appeared with her signature sunglasses and poised demeanor, prompting knowing smiles across the audience.

The moment became an instant talking point online, blending Hollywood storytelling with real-world fashion power.

For many viewers, it was a playful nod to how deeply cinema and fashion culture have influenced one another.


Jimmy Kimmel’s Political Humor Turns Heads

The Oscars have never been entirely separated from politics, and this year proved no exception.

Late-night host Jimmy Kimmel sparked conversation when he delivered pointed jokes aimed at Donald Trump and the television network CBS.

While the remarks were clearly meant in a comedic tone, they instantly grabbed headlines and fueled debates online. Political humor has long been part of Kimmel’s brand, and the Oscars stage once again gave him a global platform.

Some audience members responded with loud laughter, while others reacted with the kind of surprised expressions that make live award shows so entertaining.

Either way, the moment ensured the ceremony wouldn’t be forgotten anytime soon.


Iconic Reunions Bring Nostalgia to the Stage

Beyond comedy and commentary, the ceremony also leaned into nostalgia. Several presenters and performers reunited with former collaborators, giving longtime movie fans a sense of Hollywood history unfolding live on stage.

Oscars 2026 Highlights: Conan O’Brien Jokes, Anna Wintour Moment and Jimmy Kimmel’s Trump Dig


These reunions often become emotional highlights during the Oscars — moments where actors and filmmakers reconnect in front of millions of viewers who grew up watching their work.

For the film industry, these scenes serve as a reminder that the Oscars are not just about awards; they’re about celebrating the relationships and shared memories that define cinema.


Dazzling Performances Light Up the Theatre

Music and cinematic spectacle also played a major role in the evening’s success. The stage at the Dolby Theatre was transformed multiple times throughout the ceremony with elaborate performances tied to nominated films and musical numbers.

Each act brought a different flavor — from dramatic orchestral arrangements to high-energy stage productions — reinforcing why the Oscars remain one of television’s most visually impressive events.

The performances helped maintain the ceremony’s rhythm, ensuring audiences remained engaged during the marathon broadcast.


A Night Hollywood Won’t Forget

When the final award was handed out and the lights dimmed inside the theatre, it was clear that the 98th Academy Awards had delivered far more than just trophies.

Between Conan O’Brien’s relentless jokes, Anna Wintour’s stylish pop-culture nod, Jimmy Kimmel’s headline-making humor, and the evening’s emotional reunions, the ceremony captured the unpredictable magic that has kept the Oscars relevant for nearly a century.

For Hollywood insiders and movie fans alike, the 2026 ceremony proved once again that the Academy Awards are not simply about honoring films — they are about celebrating the culture, personalities, and moments that shape the entertainment world.

And if this year’s show proved anything, it’s that the Oscars still know how to create moments people will be talking about long after the red carpet disappears.

Entertainment

How ‘Avengers: Endgame’ Returned to Cinemas and Reclaimed Box Office Glory

Renewed ticket sales send Marvel’s 2019 finale past ‘Avatar’ to lead the all-time global chart again.

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How ‘Avengers: Endgame’ Returned to Cinemas and Reclaimed Box Office Glory

Seven years after its original release, Avengers: Endgame has unfinished business at the box office.

The Marvel Studios blockbuster has overtaken James Cameron’s Avatar to become the highest-grossing film worldwide once again. According to The Walt Disney Company’s October 4 announcement, Endgame now holds an estimated $2.9255 billion, narrowly ahead of Avatar’s $2.9237 billion. That puts just $1.8 million between two of cinema’s biggest hits.

The lead is small. The comeback, however, is substantial: a film released in 2019 has drawn enough fresh ticket sales to rewrite the all-time chart.

The ‘Encore’ release that tipped the balance

The latest theatrical run, titled Avengers Endgame: Encore, has earned $126 million worldwide, according to TheWrap. That includes $36.2 million in North America and $89.8 million from international markets—the extra business that pushed the film back into first place.

Audiences also had a reason to return beyond revisiting a familiar blockbuster. TheWrap reports that the reissue features a modified ending and three new scenes during and after the credits, connected to Avengers: Doomsday. The release therefore serves two purposes: bringing an established favourite back to cinemas and giving viewers a bridge to the next Avengers story.

ALSO READ : Emmy Nominations Announcement Gets a Star Twist… Liza Colón-Zayas & Jeff Hiller Set to Reveal 2026 TV Nominees

A rivalry with a history of reversals

This is another change of leadership in a box office contest that has lasted for years.

Endgame first displaced Avatar in 2019. Cameron’s science-fiction epic regained the crown following its Chinese re-release in 2021. Now, another theatrical return has swung the result in Marvel’s favour. Re-releases have become a decisive part of the competition, extending both films’ earning lives well beyond their original runs.

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The distinction matters: this is the record for worldwide theatrical revenue without adjustment for inflation, including re-release earnings. It measures money collected rather than the number of tickets sold.

Why ‘Endgame’ matters to ‘Doomsday’

The timing gives Marvel’s comeback an added significance. Avengers: Doomsday is scheduled to reach cinemas on December 18, 2026, and Disney has positioned Endgame as an important foundation for that next chapter.

Explaining the connection, Anthony Russo said: “You really need to pick the story up from where you left it in Endgame.”

That makes this return more than a victory lap. A film remembered for closing a major chapter of Marvel’s story is now helping introduce the next one—and, along the way, has taken back Hollywood’s most closely watched box office title.

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Entertainment

Tom Cruise’s ‘Digger’ Faces a Tough Opening: Could ‘Verity’ Take the Lead?

Cruise’s star power meets a fresh box office challenge as the Colleen Hoover adaptation emerges as a formidable rival.

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Tom Cruise’s ‘Digger’ Faces a Tough Opening: Could ‘Verity’ Take the Lead?

Tom Cruise has spent years persuading audiences to watch him attempt the impossible. With Digger, the challenge is different: convincing moviegoers to embrace an eccentric, darkly comic character who bears little resemblance to his familiar action heroes.

Directed by Alejandro González Iñárritu, the film arrives in US cinemas on October 2, 2026, carrying considerable expectations. Cruise plays Digger Rockwell, an oil tycoon confronting a catastrophe connected to his company’s actions. It is a conspicuous departure for an actor whose recent screen identity has been shaped by spectacular stunts and blockbuster franchises.

Yet the conversation before release has increasingly turned from Cruise’s transformation to a more uncomfortable question: how many people will buy a ticket?

ALSO READ : Emmy Nominations Announcement Gets a Star Twist… Liza Colón-Zayas & Jeff Hiller Set to Reveal 2026 TV Nominees

A costly film facing a modest opening

According to Koimoi’s September 30 report, Digger was tracking for a North American opening below $15 million, against a reported production cost of approximately $125 million. These are reported estimates, rather than confirmed earnings or a final accounting of the film’s costs.

That gap explains the concern surrounding Warner Bros.. An expensive production needs sustained attendance, and a subdued debut would place greater pressure on subsequent weekends and overseas markets.

An opening forecast cannot establish a film’s eventual profit or loss. It can, however, reveal how much work remains for the campaign.

Reviews have complicated the pitch

The critical response has been sharply divided. People reported reactions ranging from admiration for the film’s audacity and Cruise’s commitment to criticism of its scale, coherence and tone.

For potential ticket buyers, that creates an uncertain proposition. Cruise’s presence attracts attention, but attention does not automatically translate into enthusiasm for an unfamiliar kind of film.

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The promotional campaign has leaned into that disagreement. The Guardian described advertising that places harsh reactions alongside praise, using the controversy itself to generate interest. Whether that approach encourages curiosity or deepens hesitation remains an open question.

Why ‘Verity’ makes the weekend more intriguing

The Hollywood Reporter expects Digger to open substantially behind Verity, the Amazon MGM Studios adaptation of Colleen Hoover’s novel. hollywoodreporter.com

Starring Anne Hathaway, Dakota Johnson and Josh Hartnett, Verity is also scheduled to open on October 2. Its psychological-thriller premise centres on a writer who discovers a disturbing manuscript while completing another author’s book series.

From a marketing perspective, an established novel and a recognisable thriller setup could offer a more immediate hook. Digger, by comparison, asks audiences to take a greater leap into unfamiliar territory.

The audience verdict is still ahead

Cruise has clearly committed to that leap. At the London premiere, Reuters reported that his transformation involved prosthetics and a padded bodysuit, alongside a demanding performance.

The commercial outcome remains unresolved. Strong audience recommendations could give Digger momentum beyond its initial forecasts. A weak response would make its financial challenge harder.

For now, the film’s biggest suspense lies beyond the screen: whether curiosity about Cruise’s unusual gamble becomes an opening-weekend ticket purchase.

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‘Verity’ Could Outopen ‘Digger’: Why Tom Cruise Faces a Tough Contest

The competing releases raise a compelling question: which film will persuade more audiences to buy a ticket?

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rev 1 RGU 0170 COMP V433 INH r709g24 20260917.0086905 High Res JPEG H 2026 Daily Global Diary - Authentic Global News
‘Verity’ Could Outopen ‘Digger’: Why Tom Cruise Faces a Tough Contest

Tom Cruise has spent years persuading audiences to watch him attempt the impossible. With Digger, the challenge is different: convincing moviegoers to embrace an eccentric, darkly comic character who bears little resemblance to his familiar action heroes.

Directed by Alejandro González Iñárritu, the film arrives in US cinemas on October 2, 2026, carrying considerable expectations. Cruise plays Digger Rockwell, an oil tycoon confronting a catastrophe connected to his company’s actions. It is a conspicuous departure for an actor whose recent screen identity has been shaped by spectacular stunts and blockbuster franchises.

Yet the conversation before release has increasingly turned from Cruise’s transformation to a more uncomfortable question: how many people will buy a ticket?

ALSO READ : Emmy Nominations Announcement Gets a Star Twist… Liza Colón-Zayas & Jeff Hiller Set to Reveal 2026 TV Nominees

A costly film facing a modest opening

According to Koimoi’s September 30 report, Digger was tracking for a North American opening below $15 million, against a reported production cost of approximately $125 million. These are reported estimates, rather than confirmed earnings or a final accounting of the film’s costs.

That gap explains the concern surrounding Warner Bros.. An expensive production needs sustained attendance, and a subdued debut would place greater pressure on subsequent weekends and overseas markets.

An opening forecast cannot establish a film’s eventual profit or loss. It can, however, reveal how much work remains for the campaign.

Reviews have complicated the pitch

The critical response has been sharply divided. People reported reactions ranging from admiration for the film’s audacity and Cruise’s commitment to criticism of its scale, coherence and tone.

For potential ticket buyers, that creates an uncertain proposition. Cruise’s presence attracts attention, but attention does not automatically translate into enthusiasm for an unfamiliar kind of film.

rev 1 PRP 0290 COMP V080 DDO r709g24 20260917.0086701 High Res JPEG H 2026 Daily Global Diary - Authentic Global News


The promotional campaign has leaned into that disagreement. The Guardian described advertising that places harsh reactions alongside praise, using the controversy itself to generate interest. Whether that approach encourages curiosity or deepens hesitation remains an open question.

Why ‘Verity’ makes the weekend more intriguing

The Hollywood Reporter expects Digger to open substantially behind Verity, the Amazon MGM Studios adaptation of Colleen Hoover’s novel. hollywoodreporter.com

Starring Anne Hathaway, Dakota Johnson and Josh Hartnett, Verity is also scheduled to open on October 2. Its psychological-thriller premise centres on a writer who discovers a disturbing manuscript while completing another author’s book series.

From a marketing perspective, an established novel and a recognisable thriller setup could offer a more immediate hook. Digger, by comparison, asks audiences to take a greater leap into unfamiliar territory.

The audience verdict is still ahead

Cruise has clearly committed to that leap. At the London premiere, Reuters reported that his transformation involved prosthetics and a padded bodysuit, alongside a demanding performance.

The commercial outcome remains unresolved. Strong audience recommendations could give Digger momentum beyond its initial forecasts. A weak response would make its financial challenge harder.

For now, the film’s biggest suspense lies beyond the screen: whether curiosity about Cruise’s unusual gamble becomes an opening-weekend ticket purchase.

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