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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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31.

Lolawell    

he is a good actor, but also a jerk who deserves no attention; self deluded, hollywood egomaniac.

1801 days ago
32.

TexNess    

Carl- YOU are the one that has a homo problem. WEE ALL hope sean penn stays the hell down there, and you are MORE than encouraged to join him. You live in San Fran, right? Yep, thought so, you are a joke and a loser.

1801 days ago
33.

Jenn    

Fidel is dead you(tmz)morons!

1801 days ago
34.

p51d007    

Dear Cuba,
PLEASE keep Sean Penn

Signed,
America

1801 days ago
35.

The Seer    

Um, 23? Latinos has ONE "T" and the "L" is capitalized.

The rest of us are still unsatisfied with people in America like YOU.

And, TMZ, the point of this story is..??? SO WHAT.

1801 days ago
36.

Joanne    

I think when he goes there-- he should STAY there...

1801 days ago
37.

Sue Wong    

Cuba is a good place to visit. The USA should lift the embargo but then again I'm glad it's not full of American tourists and restaurants.

1801 days ago
38.

Whitney    

Sean Penn as a journalist? That's amazing and awesome, I'd love to hear some of his work! HTTP://WHITNEYB99.BLOGSPOT.COM

1801 days ago
39.

pincheruco    

Sean Penn is a punk, plain and simple. If he was the most intelligent, the most "buff", the most experienced, the toughest, you name it - if he was all of these things and more, he's still a punk. You can't change the spots on a leopard. Peel back the layers of an onion and what do you find - a punk!!!

1801 days ago
40.

J C    

The liberals using actors and media to brainwash and sell out the USA.

1801 days ago
41.

carlos    

Reding these kind of comments I'm really sure that most of the 80% of the northamericans citizens, who lives in USA, are incult and completely crazy. That's the main reason a similar number of persons are receiving psiquiatrich assistance... payed for them, of course. America The Crazy, not The Beautiful, is the title of your hymme.
Poor people.

1801 days ago
42.

Grouch    

Whatever he (his ghost writer?) writes will mean nothing because he is not a journalist.

1801 days ago
43.

Gapeach    

I hope he likes it so much in Cuba - he'll stay there. Maybe Castro will make him the Minister of BS.

What an idiot!!!!

1801 days ago
44.

Sarah    

Boarding a PRIVATE plane? Is this the same Sean Penn who lectures the rest of us about the environment/preventing global warming/not leaving a big carbon footprint?! Penn is a pompous hypocrite.

1801 days ago
45.

Pino    

Natalie Portman was left to fend for herself after pungent rumors that she had been defiled out of wedlock, much less with a mere “Wam Bam Thank you Mam” by not other than the “Art of Film Loving” Sean Penn.. But now he is going to exercise is lips in Cuba with the El magnifico Presidente!! Sean Penn must be very acute and selective with those outspoken loose lips of his

1801 days ago
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