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Sean Penn

Sometimes a Cigar...

10/25/2009 1:41 PM PDT BY TMZ STAFF

Sean Penn likes extremes ... he got a taste of Las Vegas Friday and Saturday and then took a flight to Cuba. The question -- is Sean gonna light one up with Fidel Castro?

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We got these pictures of Sean and company boarding a private jet from Sin City bound for Havana yesterday.

We've learned Sean is going to the land of Fidel as a journalist, writing a story for Vanity Fair about how the Obama administration has affected Cuba.

Sean took Diana Jenkins along for the ride. Actually ... it's her plane ... she's married to the head honcho at Barclays bank.

Barclays sources say Sean and Diana are going to meet Castro -- presumably because that's what Diana told them. Sean's rep tells TMZ even though the meeting is possible, there is no appointment scheduled and no current plan to chew the fat with the dictator.

82 COMMENTS

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61.

wanderer    

People should be able to live under the government that they love and choose therefore Sean Penn should stay and live in Cuba.

1823 days ago
62.

Robyn    

lol@people listening to this moron Penn who never graduated high school. Yeah he is such a smart guy. HE IS INSANE! He and all the other Hollyweird idiots need to get a grip. We need to stop seeing their bad movies and get them out of our faces. Oh yeah by the way someone said "ask Cubans what is done to homosexuals". Sean Penn is all "gay rights" and stuff like that but he's chillin with Castro. hahahahahahahahahahaha!! Dumb dumb people!

1823 days ago
63.

Z. J.    

Should be a short story. Obama has had zero affect on Cuba..or Iran, Iraq, Afghanistan, Russia, and China. Good job on the economy though, and visits the golf course more than his soldiers.

1823 days ago
64.

LensmanCT    

How do Hollywood a-holes like Sean Penn get to travel to Cuba whever they feel like it? Oh, I forgot....Liberals are above the law.

1823 days ago
65.

Bart    

That's right where that card carrying communist bastard should be. Maybe he will stay down there. Sure ain't an American and neither was his lyin' commie bastard father.

1823 days ago
66.

Duane Harbeson    

Is there anyway we can make Castro keep them.....

1822 days ago
67.

DumbassMel    

BOO! Scared of communism - funny how Amercan's like to talk about freedom (free to say/do/think whatever they want), but when a person does/say/write something they don't like, they are all worked up!
HYPOCRITES! Whatever your government tells you to do/say/think, you just follow it like sheep.
Sean can do whatever he wants, I like him,he has a brain(and he is a great actor).
Personally, I am more scared of what Diana Jenkins is wearing, she has no taste (but then she is English and they have no idea how to dress).

1821 days ago
68.

kim    

HE IS SUCH A LOSER! When is he going to realize no one cares what an actor has to say about politics.

1821 days ago
69.

Girls rule!!    

why cant he just die!!

1820 days ago
70.

Mary    

WHEN IN THE HELL IS HOLLYWOOD GOING TO STOP TAKING THEMSELVES SO SERIOUSLY? LETS SEE...YOUR JOB IS TO MEMORIZE WHAT SOMEBODY ELSE WROTE, AND THEN REGURGITATE IT CONVINCINGLY. HHHMMM, THAT'S A STRETCH. I AM JUST SHOCKED AND SICKENED AT HOLLYWOOD REALLY BELIEVING THAT THEY HAVE THE ANSWERS. IT'S LAUGHABLE AND PATHETIC.

1819 days ago
Previous 15 Comments | 1 | 2 | 3 | 4 | 5

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