Leonardo DiCaprio and the Allure of Oscar Night Chaos with Sean Penn

After skipping two important precursor ceremonies, Sean Penn may not show up to the Oscars. Let’s hope he does – so that audiences don’t lose out on his brand of chaos. Penn, nominated for his villainous performance in “One Battle After Another,” made waves at the Golden Globes before losing best supporting actor to Stellan Skarsgård of “Sentimental Value.” He then went on to win the Actor Award and the BAFTA in absentia. Given his history of skipping ceremonies – having missed three of five as a nominee – and his public contemplation of melting down his Oscars to support the Ukrainian war effort, it seems unlikely he’ll grace the Dolby Theatre, though this wasn’t confirmed at press time. This potential absence is a blow to the history of the awards and to the cause of good television.

The Lost Art of Oscar Attendance

Decades ago, winners frequently skipped the ceremony for various reasons. However, in recent years, nearly every living nominee who is physically able makes an appearance. The 2021 ceremony, affected by COVID-19, saw Anthony Hopkins unable to attend, depriving trivia enthusiasts – the Oscars’ core audience – of a memorable acceptance speech and the traditional “winning four” photograph. An end-of-night picture without a key winner feels incomplete, something undeniably missing!

Sean Penn: More Than Just ‘Something’

Penn provides far more than just a presence. While he skipped the Oscars for his first three nominations, he intuitively understood the importance of showing up for his two wins, for “Mystic River” and “Milk.” His first Oscar acceptance speech was a blend of humility and pointed political commentary, famously declaring, “If there’s one thing that actors know – other than that there weren’t any WMDs – it’s that there is no such thing as ‘best’ in acting.” He charmingly improvised, admitting his children found pre-writing a speech “presumptuous and embarrassing.”

Winning his second Oscar for portraying gay activist Harvey Milk, Penn showcased his best side, expressing hope that those who voted for California’s gay marriage ban would reconsider their stance. He closed with a heartfelt message of support for Mickey Rourke, saying, “Despite a sensitivity that sometimes has brought enormous challenge, Mickey Rourke rises again and he is my brother.” This was quintessential Penn: passionate, thoughtful, eloquent, and politically engaged. Perhaps he might bring that same energy accepting an Oscar for “One Battle!”

The Unpredictable Penn

Or perhaps he might deliver his other side, which is equally deserving of attention. His presentation of the best picture Oscar to “Birdman” – complete with an off-color joke about director Alejandro González Iñárritu’s Mexican heritage – was unfortunate, though Iñárritu played along. Before the joke fell flat, Penn was in fine form, silently reading the envelope and dramatically stretching out the “Birdman” versus “Boyhood” suspense. Another memorable moment came when he challenged host Chris Rock’s joke about Jude Law, declaring, “He’s one of our finest actors.”

Looking back, this moment is sweetly intended and humorous, showcasing the endearing self-seriousness of actors. It’s certainly not the worst reaction to a Chris Rock joke at the Oscars! It’s proof of Penn’s live-wire unpredictability. Were he to accept an Oscar, he might speak passionately about the generational struggle depicted in “One Battle After Another,” playfully criticize Conan O’Brien, or even Skype Volodymyr Zelenskyy from the stage. The point is, we simply don’t know.

An Unsettled Awards Season

This uncertainty mirrors a broader theme in this year’s awards season, where three of the four acting races remain wide open, offering potential for live-TV excitement. In best supporting actress, Amy Madigan is remembered for refusing to applaud Elia Kazan’s lifetime achievement award in 1999 due to his controversial “naming names” during the McCarthy era. Wouldn’t you want to see what she’d say onstage? The best actor field features stars like Timothée Chalamet, often compared to Leonardo DiCaprio, with his earnestness and occasional missteps. Even devotees of ballet and opera might agree that this Oscar season would be less captivating without Chalamet’s presence.

The same is true of Penn. His campaign, including an appearance on Variety’s Actors on Actors, showcased both his depth and his eccentricities before being cut short. Penn doesn’t need another Oscar; he doesn’t even care about the ones he has! But if the Oscars are to be remembered for viral moments that resonate for years to come, they might need Sean Penn.

A Variety and iHeartRadio Podcast – The Business of Entertainment