Thoughts on Sean Penn?

Solid actor but seems like a pretentious and obnoxious dickbag as a person.

Dude got buff.

I like him to extent but his work hasn't aged particularly well for me. Of his generation I prefer Cage, Rouke and Denzel. Still he is tremendous in Dead Man Walking, Milk and Carlito's Way.

As a director, I think he tries hard and follows the sort of general rulebook of Cassavetes without the magic or the humanity that Cassavetes captured as an innate characteristic of his work.

A lot of people wildly overrate The Pledge imo which has a very good Nicholson performance but is way too heavy handed and grim - it sabotages his intent for me. That applies to his whole directorial career though I did like Into The Wild.

A talented, insanely inconsistent serious actor who for a very long time happened to also benefit from being the right race and nationality, at the right place at the right time. Once the 1970's were over, a new generation of "greats" had to be annointed by the industry/media/critics. They have to be white of course, and ideally American, like those who ruled the previous decade. There were flirtations with more cerebral actors like William Hurt, but the goal was always to annoint a white American male who could obviously be directly compared to method avatars like Brando and DeNiro. In a sea of "brat pack" pretty boys like Tom Cruise, Emilio Estevez and Rob Lowe, Sean Penn with his DeNiro mimicing "method" approach stood out, even though he was still stuck playing mostly teenage roles like most of his contemporaries. Penn was the ultimate Stan/Wannabe, and he did not hide it all. He wanted to be just like DeNiro, Brando, Dean, Hoffman or any notable great american screen actor heavily associated with the method. So he cribbed from their work heavily over the course of his career.

Mickey Rourke was the other guy who had the qualities being looked at to qualify as the next "great one" for the 1980's generation, but his inability to make allies in the industry (unlike the insatiable networker that was Sean Penn) and his self-destructive attitude that killed off his career for decades, meant Penn got (wrongly) hailed the best of his generation by sheer default. At least 3 men were of his generation, even in the 80's, were better than him, but certain things put them out of immediate consideration to those searching for the next "great one". Denzel Washington (not white enough), Gary Oldman and Daniel Day-Lewis (not American enough). So Penn, despite being ridculously inconsistent throughout the entirety of his career, and despite not fully maturing as a performer till 1993's Carlito's Way, was hailed by many critics and industry folk (especially those Penn ravenously courted favor with), as the heir to the great ones that defined American movies.

There was always a massive disconnect though. Penn was one of the very few "great actors" aggressively pushed by critics onto the public, that the public couldn't quite see what the fuss was about. Critics admired his choices, as did many of his peers. Sure you could blame it on him being percieved obnoxious or irritating, but from Marlon Brando to Russell Crowe, there have been many tempermental and even outright unlikable actors (in their public personas) that the public have embraced, at least when it comes to estimation of their talent. Penn mostly just came off as a reasonably talented, but somewhat overrated actor who managed to keep himself in the tabloids on a regular basis (and that stuff doesn't happen by accident. You don't get as much press attention for non-work related stuff as Penn has without actively courting it. Penn has made it a mission to court publicity. I don't even think he cares if it's negative, as long as it allows him to stay famous).

So over the years, the disconnect has even spread to critics, as even those who once championed him finally began to question if they had been massively overrating him for so many years. So the drip,drip, drip insistence that Penn was the "best actor of his generation" has come to mostly a crashing halt in the last decade, as their is now more of a willingness to allow a Brit (DDL) and an African-American (Washington) to claim or dispute that, while Penn has found his more natural level (somewhere in the middle of his generation, not at the top).

What Penn's legacy going to be as an actor? Hard to say. He was never a good as advertised, though he's got a handful of truly excellent performances on film. But so much poor stuff as well. Penn may have had the right idea courting celebrity to the extent he has, as it may give some people who care little about his film work an incentive to check it out.

As a director, he's pretty heavy handed, though as one would expect, very good with actors (though I have yet to see The Last Face, which was supposedly a low acting point for Theron and Bardem).

I liked him in 21 Grams, didn't care for him in Milk, Mystic River, and I Am Sam.

Personally, I do not give him any wins as an actor. I really admire him as a film director, yet I still think Indian Runner is his best work imo. However, I just recently watched The Last Face & not sure what went wrong for him. Film was too long & the two leads were just wasted. Did not feel like a Penn picture at all. Still, I am confident he can go back to his original roots. 

Is there any buzz on Flag Day?

Definitely a great actor. His work in some movies (like Milk ie) is incredible.

Does he deserve two wins though? Highly doubt it.

pacinoyes Toughts of the other B-Day boy Sean Penn ?

This Flag Day tour is weird. It's like he's acting like he's still a celebrity.

I agree, but this is sad.  Into the Wild was really good and not that long ago.  But dude has no self-awareness.