What do you think of Sean Penn's looks?

As a rule I don't think about Sean Penn

He's never been a looker. Not with that nose.

R2, what's wrong with his nose?

Never thought he was attractive always thought he was quite a douche.

It's too big in comparison to the rest of his facial features, R3.

When he was with her.

He looks kind of cute here. Madge is a mess (rebel gone wrong).

Troll

Movie stars often have large noses compared with their other facial features. For some reason it films well, I have no idea why. It's almost a requirement and it's often why actors who get nose jobs that go too small fuck up their faces and fail.

Sean Penn is a hell of an actor. A HELL of an actor. Not a lot of people saw his Willie Stark in "All the King's Men" but in that film Sean Penn does a transformation within a scene, sans any makeup or other tricks, better and more convincingly than I've ever seen in my life (and I'm old).

He's brilliant and I really don't give a shit about his personal life.

Not my type, but he looked best in At Close Range.

A very young Sean Penn appeared in an episode of Little House on the Prairie in the early 1970s, the episode where the town kids get together to create a new bell for the school/church. He's a background town kid, not a speaking part, he has his long blonde hair, distinctive face, wearing overalls. I believe his father was the director or other creative participant on that particular episode, so that's how he came to appear on it. Just thought I'd mention it. :-)

He ALWAYS looked like Freddy Kruger to me especially as he's aged. I can't believe others(especially Madonna) don't see it

Like most people, he looked his best when he was young, long before he got perma-tanned and his inner douche became evident. Around the time he was with Madonna was probably his physical peak.

He always had moments where he would look good but then other times not so much.

Be still my heart 🙄

The high school bully with the permanent scowl on his face and the chip on his shoulder doesn't work for me either

No way, R9. His schnoz is not attractive and it's so big in proportion to the rest of his face that it's distracting.

R16 Pic makes Sean Penn look sexy and alluring at that time, like a plumber showing up to clean your pipes, working class, average looking Joe with a regular face, but still sexy and appealing, in that photo. He's older now, so... :-/

^ Some people find the brooding bad boy attractive... I find him annoying. He'll take your money, break your heart and in retrospect you'll realize he wasn't all that good in bed

Looked like Montgomery Clift when younger

Don't think so. Montgomery Clift was much more attractive.

Irish-Italian tough.

ugly AF. like a rodant that contracted the pig pest and had a cyst boil in the nose

R20 you should book an appointment with a good ophtalmologist ASAP

He's always been hideous and you can tell he smells bad

Always found him flat out ugly.

What all makes him ugly?

I don’t find him that attractive, and I also am someone who likes big noses (Adrien Brody could fuck me with his schnoz for all I care—I’d enjoy it).

Here, with moustaches

Personally, I never found him all that attractive. Just not my type. When he was young I thought Robert Mitchum and Kirk Douglas had had a baby.

R12, what makes him look like Freddy Kruger?

He looked ok in the Woody Allen movie.

At Close Range.

He’s not a looker but he holds the screen.

Early 40s - 2000-2005.

He’s always been homely. And overrated as an actor. Humorless cuntrag.

He's actually Irish-Jewish descent, R22, which can be a very sexy mix (eg, Harrison Ford).

Second At Close Range

He should of played Freddy Kruger. He is an atrocity, period. No way he got a start without connections.

^^^ He should have played.....

@r37, I never new Harrison Ford was part Jewish and I grew up in the same town and went to the same school 🤔

R39, most likely via his father…

He always looks dirty. So does Madonna. They were perfect for eachother.

He looks like an angry turnip.

I am well aware that he’s an asshole. But when I was younger, before I understood his personality, I thought his male energy was sexy AF. He was as masculine and alpha as they came, and I thought that was incredibly sexy. I also love that he doesn’t look like a male model/perfection, I’ve never found pretty boys to be as attractive,

He had a perfect face in his prime.

The first movie I saw him in was Bad Boys. He was outstanding.

R37 There's Italian in there too, through the mother.

[quote]He looks like an angry turnip

LOL R44.

He defintitely had his moments in the 80/90s. Like r45 said, he had a certain sex appeal onscreen and the right amount of cockiness. He's had a lot of women so he clearly had something. But now, he just looks sleazy and burnt.

I think his brother Michael looks better now.

He looks like an apple that’s been left on a radiator.

I kinda liked him in Dead Man Walking...

He had a certain swagger.

I think he looked his best in the late '90s.

When he was with Madonna was when he looked his best.

[quote] What do you think of Sean Penn's looks? And when do you think he looked his best?

Ah…..never?

will cop to finding him sort of MILFy hot in The Thin Red Line but i'm completely deranged about that movie in general so :/

What do you think of his looks here? :

He looks a lot better when he's in character, like he did as Harvey Milk.

He definitely looked best when he was with Madonna and in the film, At Close Range.

R58, I can definitely see how he could be someone’s type —dark and brooding.

He’s just not mine.

He was always handsome

I always thought he was kind of ugly-hot. He could clean up well but didn't seem to care about his looks and often seemed to seek out parts where he could be unattractive. Agree that At Close Range was probably his peak sexiness.

R51 for the win.

Looks aside, "The Gunman" in on my list of Bad (Not in a Good Way) movies.

Even Mark Rylance, who I adore, is embarrassing to watch probably because he himself looks embarrassed.

Now that I think of it, I can't think of a vanity flick that's ever worked.

when he was young he was cute-rough-charming. A face with character.

[quote] He looks kind of cute here. Madge is a mess (rebel gone wrong).

Madge made him attractive otherwise he was not cute. I first saw him in "Taps." Tom Cruise never looked worse and even he was better looking than Penn.

Looks like Rob Lowe

He looks like a 7-11 hot-dog that has been left on the rotating grill for no-one-knows how long.

I always thought that he was ugly. If Madonna married him, he must have a big cock or eat pussy like a pro.

He was hotter than hell in At Close Range. But he didn't age very well, and looked grizzled and old by the late 90s. Definitely looks older than his years, I assume from hard living, drinking and smoking, etc.

He looks like an ashtray. I wonder when he'll get emphysema or lung cancer

[quote] And when do you think he looked his best?

He's beautiful as NEVER.

Handsome even in school:

I'm sorry, to me he's always looked like the type who you'd see in an old picture of a lynch mob, like you wouldn't be at all surprised to discover in the dead of night he'd firebombed a Black church or burned a cross on an interracial couple's property.

Yuck.

m3 = Rossy de Palma

That's one ugly broad R74

I found him hot until right after Milk. Now he looks like my dad.

Ugly

Never

What features make him ugly?

[quote] What features make him ugly?

His elbows, Rose.

Is he the best actor ever?

Yes R82. Just like Condi Rice is the most beautiful woman ever.

Always thought he was flat out ugly.

He was always ugly to me…beady eyes oversized nose…nope…never

He looked pretty hot in the movie The Gunman from about 10 years ago

He was ugly when young but in the early 2000s he had this raw masculinity on film that was very appealing.

r86 that isn't hot. to each his own. That's gristle and possibly fuckable. But scary old skinny fit man fuckable.

Keisha, gurl, he busted.

He’s never been handsome. But a great actor.

He's beautiful from the neck down, like Loni Anderson.

I thought his late kid brother Chris Penn was cuter.

Ugly on the outside, ugly on the inside.