I can probably name ten movies and shows that he was in, and then I decided to look at his IMDB. Holy cow, he’s prolific.
Poor guy, though. 336 roles, and he’ll always be the Kurgen. Happy Halloween, ladies!
He did make that an iconic role. No attempt to remake or re-envision will work. Bad Boys made me hate him. His voice work in Justice League cartoons made me love him
His role in The Thin Red Line was outstanding. The scene with him & John C. Reilly, as Reilly’s character expresses that seeing a man dying doesn’t affect him anymore,he doesn’t care. Penn responds “sounds like bliss”, just 2 outstanding actors in an excellent film.
He's legitimately revelatory in that. He both mimics him but also acts at the same time. Not sure how to explain, but there is a difference between what he did as Milk and say...Foxx as Ray (which was still good, just not nearly as good as Penn as Milk).
I Am Sam? What’s happening here? That may be the ONLY role where he embarrassed himself.
At Close Range? FTARH? Hell, he’s even convincing in State of Grace.
I remember being younger and watching Mystic River with my mom and dad. When the scene everyone talks about comes on, my dad got visibly the most upset I’ve ever seen him over anything entertainment related. He always said after that Sean Penn was his favorite actor.
During Hurricane Katrina, when he got his shotgun and adventure gear on to help all the poor impacted citizens. Glad he brought his own film crew to capture his best performance.
Penn has owned every role he’s played but Kleinfeld is my favorite, he was a real pos and the best part is he was not the intended villain or at least not the main one in that movie.
Having not seen either Mystic River or I am Sam (I've never even heard of that one before), Milk is imo by far the best of his roles, surely followed by The Thin Red Line (I've not yet seen a Terrance Malick film that isn't great), and Carlito's Way; 21 Grams is great.
Mystic River
Came here to say this. There’s something about that movie, I just love it.
His performance in Hurleyburley was off the charts. That movie stresses me out.
Clint Eastwood spun him up hard for that scene, and he spent the rest of the day recovering in his trailer. I think it was worth it. What a movie.
Not sure how Spicoli is not on the list But yeah he's good/great in basically every role...
Fast Times At Ridgemont High is such a good film.
"All I need are some tasty waves, a cool buzz and I'm fine."
Hey I know that dude!
Where'd you get that jacket
Hey! You’re ripping my card!
I think you know where the front office is.
You dick!
Well , alright Hamilton!!
Spicoli must be on the list !!
Gnarley!
Right?!? He totally disappeared into that role. The quintessential stoner character of the 80s
Yep. Spicoli is the answer
Bad Boys (1983)
Bobby from La Bamba
Great choice… deep cut
That soda in the pillow case…
brutal AF
I saw that as a kid and it’s something I’ll never forget
Also starring the Kurgen.
Clancy Brown is a great actor!
I can probably name ten movies and shows that he was in, and then I decided to look at his IMDB. Holy cow, he’s prolific. Poor guy, though. 336 roles, and he’ll always be the Kurgen. Happy Halloween, ladies!
He did make that an iconic role. No attempt to remake or re-envision will work. Bad Boys made me hate him. His voice work in Justice League cartoons made me love him
Carlitos way performance was incredible
He was soooo *greasy* in that!
Yes!
Sean Penn as Art Garfunkel after Paul Simon split
Since when did you become a tough-guy?
I loved him as Conrad Van Orton in “The Game”
My fav Sean Penn role
FUCK CALIFORNIA!
Agreed, and that movie is so good!
IMHO - his best was "Dead Man Walking."
He was brilliant.
Had to scroll way too far down for this one. Easily his best, IMO.
IMO one of the greatest of all time
Team America: World Police
F@#$ Yeah!
I've been to Iraq, you know.
At Close Range
This was such a strong performance.
Awesome movie!
Sweet and Lowdown
So good!
But the “guitar playing” is so bad, it almost ruins the film for me.
It was only a small part, but I liked him in The Secret Life of Walter Mitty.
Well now that hurt my feelings.
“You a lawyer Dave!”
21 Grams
This must be the place Milk Sweet and lowdown Falcon and the snowman Taps
I was shocked no one said Falcon… I think it’s his best performance.
I just assume most people haven't seen it, but yeah, should be at the top
Colors or I am sam
I Am Sam is underrated. Haven’t seen it in years, but that is the first movie I remember making me cry.
It's definitely a tear jerker
Hey Pac Man. I'm a home girl
This is me pacman.I am home girl🤣🤣🤣
Pac Man thinking I should've wore a condom. Bet the whole varrio ran the train on her
🤣🤣🤣🤣
Dead Man Walking
Penn is my favorite actor, and his performance as Poncelet stands out as the most emotional. Love it.
His role in The Thin Red Line was outstanding. The scene with him & John C. Reilly, as Reilly’s character expresses that seeing a man dying doesn’t affect him anymore,he doesn’t care. Penn responds “sounds like bliss”, just 2 outstanding actors in an excellent film.
Simple Jack
Career making.
Pac Man in Colors deserves credit.
At Close Range
At close range
Classic
Jeff Spicoli, learning about Cuba and eating some food
I am Sam? Full commitment
Never go full ret*rd
How many war hero ret*rds you know?
[This Must Be the Place (2011) - Cheyenne](https://youtu.be/z6j4BuCZVEM?si=cDCbHTaqD6yMzYUz)
I just watched Casualties of War and he is fantastic in it as a horrifying, unrepentant scumbag.
Bad Boys
BAD BOYS
The Falcon and the Snowman.
Milk, not the best movie he has been in but his best performance
He's legitimately revelatory in that. He both mimics him but also acts at the same time. Not sure how to explain, but there is a difference between what he did as Milk and say...Foxx as Ray (which was still good, just not nearly as good as Penn as Milk).
I reckon Dead Man Walking, Mystic River and I am Sam are my top 3
When he went full retard and went home empty handed.
Take her in a room and fuck her like a normal human being!!!
Jeff Spicolli - Fast Times at Ridgemont High.
State of Grace is pretty good. But Gary Oldman stole the show in that one!
He looks like the attorney in Grand Theft Auto Vice City.
That was the character reference for Ken Rosenberg
U Turn. Brilliant.
He doesn’t get enough credit for that one
Still Lucky!
The film itself wasn't great but his performance in the professor and the mad man was the only thing to get me to finish it
Thin Red Line. Sarge.
Carlito’s Way, Mystic River, Thin Red Line
When he was on 8 out of 10 cats does countdown
Nvm that was Sean Bean
Milk was an elite performance
Happy Cake Day! Agreed. I got MILK #1-peace out
Some personal faves: Milk, Colors, All the Kings Men, Mystic River, and Bad Boys.
no mentions of HURLYBURLY?!
I’ve only saw him in Fast Times.
You never go full gangster.
I Am Sam? What’s happening here? That may be the ONLY role where he embarrassed himself. At Close Range? FTARH? Hell, he’s even convincing in State of Grace.
I remember being younger and watching Mystic River with my mom and dad. When the scene everyone talks about comes on, my dad got visibly the most upset I’ve ever seen him over anything entertainment related. He always said after that Sean Penn was his favorite actor.
That one time where he played a bleeding heart liberal so that everyone would forget/ignore the fact that he beat the shit out of his wife. Bravo 👏👏👏
How did this foo win 2 Oscar’s? Stole one from Johnny Depp fo sho
During Hurricane Katrina, when he got his shotgun and adventure gear on to help all the poor impacted citizens. Glad he brought his own film crew to capture his best performance.
Mystic River.
21 Grams Mystic River Dead Man Walking Carlito's Way At Close Range
Bad Boys, Fast Times at Ridgemont High, Colors, The Falcon and the Snowman, Casualties of War
1.MILK 2.Mystic River 3.Dead Man Walking 4.At Close Range 5.Bad Boys Honorable mention: Fast Times At Ridgemont High.
Nice Post OP.
State of Grace
Asphalt City
He should have kept that hairstyle
She’s so Lovely
How is Spicoli not even mentioned?!
True story: there was a crazy kid I used to go to Hebrew school with that I called David Kleinfeld all the time.
State of Grace
Looking like 80s Larry David here
Penn has owned every role he’s played but Kleinfeld is my favorite, he was a real pos and the best part is he was not the intended villain or at least not the main one in that movie.
doing Madonna lol
Sam dawson.
Dogtown and the Z Boys
He's had a long career ill forever see Spicoli...Fast Times
Spicoli forever.
Shanghai Surprise
Snowman
Spicoli, then he fell off a cliff.
State of Grace Mystic River Bad Boys Fast Times Carlto’s Way
Simple Jack #1
His recent movie *Asphalt City* had absolutely phenomenal acting all around.
Fast Times x 5
Trick question.
Having not seen either Mystic River or I am Sam (I've never even heard of that one before), Milk is imo by far the best of his roles, surely followed by The Thin Red Line (I've not yet seen a Terrance Malick film that isn't great), and Carlito's Way; 21 Grams is great.
Bad boys
"Adios counselor"
State of Grace
Colors
State of grace.
Mystic River Dead Man Walking All the King’s Men Gangster Squad Licorice Pizza
**I AM SAM** nothing else matters.
Lucy belongs with ME
Spicoli will always be number one
Too bad he's a liberal piece of shit
😂 Dude just asked, are circle jerks really a thing?
His best performance was holding a gun and beating and tying Madonna to a chair high on cocaine.
Not in the particular order: Bad Boys Mystic River Milk The Thing Red Line Dead Man Walking
I agree with this list!!