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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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1.

Carl    

In before right-wing nut jobs ranting about Sean Penn.

1824 days ago
2.

pizza    

Nothing in Sean Penn's body of work or personality or intellect warrant giving any attention to anything he does.

1824 days ago
3.

Thomas    

Gees, I'll bet that story will be objective! He should write it on toilet paper. At least the story will have a purpose then!

1824 days ago
4.

UGGGGHHH    

HE JUST NEEDS SOME ANGER MANAGEMENT.

1824 days ago
5.

Stinker    

That commie should marry jane fonda and then be deported to cuba.
I hear he goes down there so he can get drugs to smuggle into the USA.

1824 days ago
6.

MaBaBah    

A good question would be, why would they choose Sean Penn and not a real journalist? Maybe some softball questions? Maybe so he writes exactly what he is told?

It is little more than a fifth graders 'how I spent my summer' report.

1824 days ago
7.

kgb    

So the head of Barclay's Bank's wife is the weirdo wearing a loose, see thru' bath towel and a boob bandanna walking onto the plane? WOW. A couple of rocket scientists on a journey to no where about nothing.
It will be interesting to hear Sean's cutting edge report to see how the Cuban's lives have improved since OBAMA...because my life, a born and bred American has NOT IMPROVED one bit and I am risk for losing more of my hard earned money to pay for more stupid taxes..and by the way WHERE THE HELL IS MY SWINE FLU SHOT? Obama scares the crap out of us with the pandemic announcements...yet his sytem is so lame..we sit no help...

1824 days ago
8.

arte help    

Hey Carl, maybe you can give him a h*ndjob before he leaves!

1824 days ago
9.

jerry    

Mauricio SHOGUN Rua got ripped off last night...

He beat Lyota Machida. What a disgrace.

Those 3 judges need a kick in the nuts. IDIOTS.

Great performance SHOGUN.. You are the champion.

1824 days ago
10.

pinky    

Why would anyone read anything written by Sean Penn?
I feel sorry for his family....

1824 days ago
11.

Professor Obvious    

Rush Limbaugh says Penn is a communist that will do anything to destroy America. As a lifelong Republican, I believe in Rush and hope Penn dies in a fiery plane crash. I don't want penn to destroy my country.

1824 days ago
12.

jeezlouise    

Because Sean Penns opinion is so important. Whatta f-ing a$$hole.

1824 days ago
13.

Carl    

Hey Tkennedy,

Despite your homosexual fantasies, you've only helped prove my original comment correct.

1824 days ago
14.

ginko    

I hope sean penn and carl end up like penn's brother! F-in loser commi's

1824 days ago
15.

JT    

Hmmm... I thought Americans were not allowed to go to Cuba... damn, better book my holiday there before the floodgates open.

1824 days ago
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