Sean Penn's Oscar for Milk

Well, in many ways you could call it his best. It's his most complete portrayal at least - and by that I mean he often gave great "half" of performances where he made part of a character work so well, you ignored what he didn't do well. You gave Sean Penn a longer leash with criticism at one time than you would have with his 80s peers or most actors even......

Milk is a totally effective performance across many behavioral characteristics which makes it very surprising that he gave it - it's sorta like Will Smith this year - where he checks off so many "acting" checkboxes he makes the competition look like they're only playing "1 thing" - whether it's actually true or not.........it "appears" true.......that's why he won and it's not usually his strength.

One thing he does really well in that movie is modify his voice and manner of speech depending whom he's talking too......he's also great at not weakening Milk - he's not a pushover - he's "dealt" with bullies all of his life.

Now I'll tell you, that when he got that 2nd Oscar (presented to him by some De Niro dude) he was the best American film actor of the 80s generation at that point - now he's been surpassed by Washington, Hanks, and some others too you could argue (Cage, Dafoe) but that doesn't diminish what he was.....he is no different from Dustin Hoffman in 1988 who was later surpassed by DePac, Nicholson, Hackman (very arguable with Gene, not quite to me) ........that happens, and that's ok.......and also btw it's not Sean Penn's fault Mickey Rourke didn't win.

Ask Peter Fonda and Michael Keaton what the Academy thinks of 55-60 + year old men without any Oscar nominations getting their first Best Actor nod......it's like I said above - the Penn performance will always beat Rourke anyway though - always - it's that "checks the boxes" thing......

I usually like Van Sant but this one doesn't work for me. The whole thing is your standard middlebrow oscar-bait biopic. Penn's performance is not "bad" but also unremarkable. He's doing a fine impersonation but that's it; just a surface-level work. He's also not even the MVP of his film (which is Brolin).

It is also one of my least favorite wins but I like that he gave a special shout-out to Rourke, the actual deserved winner of the night. I guess even he wanted Rourke to win.

Not good. He completely nailed Milk's technical mannerisms, but it left no impression whatsoever. Poor script. Emile Hirsch was better in the movie. Leo much better in Revolutionary Road. Pitt better in Benjamin Button. I wasn't aboard the Rourke hype train at all, though.  Was glad to see Penn box him out.  

It's alright. Solid bit of technical mimicry, but as has been mentioned, surface level stuff. Should never have won the Oscar, but at least it much better than his first one for Mystic River.

Penn was never the best film actor  (American or otherwise) of his generation.  He was always a hugely inconsistent performer with some talent, since Day 1. He was more or less a hype job that critics and the industry came behind,  but audiences saw through and never supported. I could see why other actors admired him. He copied/mimiced the right "greats" and sold himself aa a beacon of "artistic integrity ". You do enough arthouse stuff they like and  critics will often treat you like a God, regardless  of your talent level (see Kristen  Stewart). He was never as good as they wanted him to be. Which was to be the great white hope for the 80's as the heir to the method crown of Brando, Hoffman, DeNiro etc,  especially when the much more talented other white hope of the  80's Mickey Rourke proved too volatile and entered the 90's with few industry allies and a wave of bad choices. The alternatives were the new wave of more shallow-seeming pretty boys like Tom Cruise, Matt Dillon or Rob Lowe. Penn came off more serious than them, even though he was even a lesser talent than Val Kilmer (who was underestimated during the whole of the 80's,  in part due to his pretty boy looks also).

The real greats of his generation (Daniel Day-Lewis, Denzel Washington and Gary Oldman...though Oldman was more character actor than leading man like the others) that also had method styling were either too British or to ummm....non-white to be declared the next Brando/DeNiro/Pacino etc, so they didn't recieve the wave of hype Penn got in the 80's and then 90's with those comparisons, even though all of them were far more talented and accomplished than him at every step of their careers. It needed to be a white American to ride that hype train, and as very obvious slaves to method actors of the generations before, Penn and Rourke made the most sense to hype (though I'd argue at least in the 80's,  at least Rourke deserved the hype .I don't think Penn gave any particular  special performance on film till the early 90's in Carlitio's Way (probablyhis best performance). Everything  before that was mostly method posturing from a young actor trying to mimic much better older actors).

Watching Oldman blow Penn off the screen in State Of Grace made me wonder how he was ever rated the best of his generation (for awhile anyway) by some critics. Washington and DDL also always obliterated him from the beginning.

They also never courted close friendships to past legends like Penn to gain endorsement. who was tight buddies with everyone from DeNiro and Brando to Jack Nicholson. As good friends do, they would always hype him up as well, which is to be expected 

I always saw through the hype, which now seems hard to imagine, as an entire generation of cinephiles since 2008 has been born and are of age, who don't realise Penn was once ever that highly regarded. He used  to give a lot of bad performances he deserved all the Razzies for All The Kings Men, Shangai Surprise etc . And I found his mumbling method posturing in Casualties Of War tedious, though it has some fans. The less said about I Am Sam, the better), and highly  overrated ones (though he was legitimately brilliant  in a few things like Carlitio's Way and Dead Man Walking). I used to predict since the early 2000s  that he would go down as the Rod Steiger of his era (wheras, his supporters always tried to sell him like he was the new Brando of our time) .Looking at how far his career has fallen since his 2nd Oscar, I' d say comparing him to even Steiger (who was also a more gifted actor than Penn) might be unfair to Steiger. 

As the whole former "best actor of his generation " stuff has long since faded into memory, while generational peers like Washington and DDL ascended to GOAT status and left him in the dust, it's still quite impressive that he retains a lot of his celebrity. He does whatever he can to stay in the press and stay famous.  His public pronouncements (the latest one saying cowardly  genes make men wear skirts )and publicity seeking are infamous. I think he's arguably the least talented of the major group of stars heralded among the best of his generation  and that is why he has faded so badly and is struggling to give another major performance in almost 14 years. He's a great Hollywood Networker (only matched by George Clooney, imho), so I think there still exits the possibility of him giving another major performance (an insignificant turn in Liquorice Pizza was never going to cut it(.  But it's a real struggle for him). And he's trying to make-up and bald cap his way to some TV acclaim with that new Julia Roberts vehicle  Gaslit...which may or may not work. But he was always lucky to be the right guy at the right time to be propped by critics for as long as they did. And when they stopped excusing his inconstency  and sheer volume of poor performances, the jig was up.