Prior to 2026, only three actors had ever won three different Academy Awards for acting, but now, we have a fourth in Sean Penn, who made history when he got his hands on a ‘Best Supporting Actor’ statuette for his role in One Battle After Another.
Well, he didn’t actually get his hands on it as he wasn’t at the ceremony, but it still counts, even if he couldn’t be bothered to show up. However, the 2026 Oscars sum Penn’s character up perfectly as the clearly extremely talented, versatile performer who can disappear into pretty much any character at the drop of a hat, but, at the same time, he is seriously unlikable.
There’s something about him that exudes arrogance, that he knows just how good he is and thinks he can get away with anything. While he supports a lot of good causes, he does so in a way that feels preachy, and his history is littered with strange on-set behaviour and more than a few real-life controversies, making him a deeply polarising figure.
It turns out that there has always been a pompous streak about Penn going all the way back to the start of his career, where in an interview with UPI, he revealed that he had to overcome his own ego to get a foot on the ladder.
“Long before I had a penny in my pocket, I had a kind of feeling of entitlement as an actor,” he explained, “Not because I thought I was so good, but because I thought the rest were not so good. That gave me an awful lot of confidence…I resented every audition, hence I was terrible at it and self-conscious.”
This was even true of Fast Times at RidgemontHigh, one of Penn’s first big breaks, about which he admitted, “I just wanted them to just give it to me. I auditioned, and terribly and flat. I knew I wasn’t willing to hit the kind of music of this character that I thought it was and had familiarity with too.”
Luckily for the young star, director Amy Heckerling saw through this boastful swagger, and Penn was cast as Jeff Spicoli, the main character, who, similar to his actor, considers himself an expert in a particular field (surfing) despite having no demonstrable proof or evidence.
As it turns out, giving Penn a chance to prove himself was a very good idea, as Fast Times at Ridgemont High was a huge sleeper hit, still serving as a blueprint for the teen comedy and was absolutely packed with future stars. Alongside Penn, it also gave a leg-up to Nicholas Cage, Forest Whitaker, Eric Stoltz, and more, apart from also being the first film ever written by the great Cameron Crowe.
Arrogance is an extremely volatile quality, especially for actors, where, while you need to have confidence in yourself in order to succeed, taking this too far can cost you opportunities. Penn was lucky that somebody decided to take a chance on him; otherwise, he might have ended up just another arrogant young man with nothing to show for it.
