A Lingering Image from the 2026 Oscars
Six weeks after the 2026 Oscars celebrated Hollywood’s finest, one image continues to linger in my mind from the past year of films. It isn’t Jessie Buckley’s haunting wails of grief in Hamnet, or Amy Madigan’s diabolical, lipstick-smeared grin in Weapons, or the remarkable whirling blues soundtrack of Sinners. No, it’s the image of Sean Penn as Colonel Steven J. Lockjaw in the best-picture-winning One Battle After Another, smacking his lips and sucking his teeth constantly, for absolutely no reason, on his way to a victory for best supporting actor. It’s unfortunately emblematic of the past four decades of the Sean Penn experience: self-indulgent, over the top and critically acclaimed.
The Oscar-Winning Paradox
Only eight actors in Hollywood have won three or more Oscars – it’s a who’s who of the greatest thespians to appear in film: Katharine Hepburn, Ingrid Bergman, Jack Nicholson, Meryl Streep, Daniel Day-Lewis, Frances McDormand … and now, somehow, Sean Penn. Penn is not a terrible actor per se. He’s a strong on-screen presence: compelling, or at least hard to look away from. But he’s a scene-stealer for all the worst reasons, a serial over-actor who repeatedly mistakes intensity for depth, and contorted features and shouting for emotional range.
A Promising Start, a Declining Path
Penn was a promising talent in the ’80s, even if a rewatch of his breakout roles shows early signs of the caricature that has only become more pronounced in the decades since: his goofy, stoned surfer-dude in Fast Times at Ridgemont High, going toe to toe with Christopher Walken in the crime drama At Close Range.
But as he gained in fame and esteem, he completely lost sight of the ground. His performances became increasingly hammy and exaggerated, scenery-chewing without self-awareness, psychological complexity replaced with sheer strain. He shouted and wheezed and contorted his face in any number of distracting visages and called it acting. We all called it acting. To the tune of three Oscars.
A Questionable Legacy
Granted, it’s not like he’s Tommy Wiseau. He’s Nicolas Cage with a better agent. But where Cage’s expressive mania became more meme than man (before his recent career renaissance), Penn was showered with praise. He is a testament to choosing the right projects and doing just enough to ride the coat-tails of auteurs to greater heights, rather than taking any old schlock just so he can afford to buy a massive dinosaur skull.
It’s like he studied at the Al Pacino school of film acting but, like his own Jeff Spicoli, missed a few key classes: skipping out on The Godfather and Dog Day Afternoon, straight to “Say hello to my little friend!” and “HOO-AH!”
Notable Performances and Controversies
His first best-actor win was for Mystic River, a near-perfect crime drama of which Penn is the hardest part to watch. Grieving father Jimmy Markum is the role of a lifetime, complex and challenging and raw. In Penn’s hands, key moments border on farcical. As he bellows and screams, “Is that my daughter in there?” it’s hard not to hear, “Is that my Oscar in there?”
Similarly, in last year’s One Battle After Another, a potentially interesting antagonist is comically overshadowed by a series of bizarre choices: all distracting physicality and cringy facial tics, limping quickly and barking loudly. Next to co-stars Leonardo DiCaprio and Benicio Del Toro, he’s a cartoon character parachuted in from another (much worse) movie.
His lead role in Milk, as Harvey Milk, the first openly gay man elected to public office in California, is his most nuanced performance, and even then he still can’t avoid lapses into effeminate gay stereotypes. And the less said about his effort in 2001’s I Am Sam the better – a deeply offensive and absurdly terrible performance as a father with an intellectual disability that should have been widely panned, and yet, guess what? Another Oscar nomination!
A Life of Self-Importance
As reflected in his real life, where he has inexplicably inserted himself into several global conflicts and met with several world leaders, Penn is Main Character Syndrome taken to the nth degree. His acting is always Very Serious, foot to the floor, no matter how tight the turn. It’s like his performances have a separate identity to the movie they appear in, the centre of a galaxy that the plot and other characters aren’t orbiting. Restraint be damned. Rapturous applause to follow.
As Colonel Lockjaw would say, probably while sucking on his teeth for no reason, “What is that? Some kind of sick joke on God?”
Find out the next TV, streaming series and movies to add to your must-sees.
Get The Watchlist delivered every Thursday.
