2026 Oscars: Burning Questions – Sean Penn, Surprises & More

The 98th Academy Awards are just days away, and as the excitement builds, several key questions remain. Will Sean Penn, fresh off a win at the Actor Awards, actually appear on the Dolby Theatre stage? And who will have the honor of announcing the Best Picture winner this year?

A No-Show Streak? Penn’s Awards Season Approach

Sean Penn’s path to potential Oscar glory has been…unconventional. Although he’s now considered the frontrunner for Best Supporting Actor for his villainous role in Paul Thomas Anderson’s One Battle After Another, his attendance at awards shows has been spotty. He skipped both the Critics Choice Awards and the BAFTA Awards, despite winning at the latter. This follows a pattern of selective appearances; he did attend the Golden Globes, where he was also nominated, but has largely remained out of the spotlight for One Battle compared to his co-star, Leonardo DiCaprio.

DiCaprio himself was absent from the Actor Awards due to filming commitments with Martin Scorsese, suggesting a busy schedule is at least partially responsible for these absences. As of now, it remains unclear whether Penn and/or DiCaprio will attend the Oscars ceremony on March 15th. Gold Derby has reached out for comment, but has yet to receive a response.

The Fab Five and Potential Presenting Pairings

Beyond Penn’s attendance, speculation is swirling about who will present the coveted Best Picture award. The Academy has a history of choosing iconic figures or memorable pairings for this honor. Recent presenters include Billy Crystal and Meg Ryan (for Anora in 2025), Harrison Ford (for Everything Everywhere All at Once), and Lady Gaga with Liza Minnelli (for CODA).

One intriguing possibility is a reunion of sorts, potentially involving Neil Diamond. The film KPop Demon Hunters, featuring a song penned by Diamond, is a strong contender for Best Song and Best Animated Feature. Given Diamond’s Parkinson’s diagnosis in 2018 and subsequent retirement from touring, his appearance would be a particularly poignant moment.

Will Conan O’Brien Bring the Comedy?

The Oscars are also known for their comedic moments, and Conan O’Brien’s hosting gig last year set a high bar. He famously emerged from a The Substance-inspired reveal and performed alongside a sandworm from Dune: Part Two. The question now is whether he’ll reprise a similar stunt this year, perhaps with a bit focused on characters from 2025’s contenders. Specifically, there’s speculation he might riff on Amy Madigan’s character from Weapons, DiCaprio’s role in One Battle After Another, or the twins from Sinners.

The “Fab Five” Format: A Potential Return?

Another popular format the Academy has employed is the “Fab Five,” where five past winners from a category present the award to the current nominees. This format, which debuted in 2009, was tweaked last year amid controversy surrounding the film Emilia Pérez. The Academy shifted the focus to presenting craft categories with famous faces rather than acting races. Whether the original format will return this year remains to be seen, but it’s a fan favorite known for its authenticity.

Record-Breaking Potential for Sinners and One Battle After Another

The 98th Academy Awards could also witness a historic night for either Sinners or One Battle After Another. With 16 and 13 nominations respectively, both films are within striking distance of breaking the record for most Oscar wins, currently held jointly by Ben-Hur, Titanic, and The Lord of the Rings: The Return of the King. Gold Derby’s predictions currently favor Sinners to reach this milestone, leading in 13 categories, while One Battle is a strong contender in 10.

International Films Making Waves

This year also saw a surge in recognition for international films. Sentimental Value and The Secret Agent both landed in the Best Picture lineup, and Sentimental Value is predicted to win Best International Feature. While it’s unlikely an international film will win in any other category, the increased representation marks a significant moment for global cinema.

As the Oscars draw near, the anticipation continues to build. The ceremony promises to be a night of suspense, celebration, and perhaps a few surprises. Whether Sean Penn will grace the stage, who will present Best Picture, and which film will build history remain open questions, adding to the excitement of Hollywood’s biggest night.