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10/25/2009 1:41 PM PDT BY TMZ STAFF
Sean Penn -- Sometimes a Cigar...

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.

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Reader Comments

(Page 1 of 5) | 1 | 2 | 3 | 4 | 5 | Most Recent | Next 15 Comments
1.

Carl:  839 days ago

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

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2.

pizza:  839 days ago

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

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3.

Thomas:  839 days ago

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!

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4.

UGGGGHHH:  839 days ago

HE JUST NEEDS SOME ANGER MANAGEMENT.

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5.

Stinker:  839 days ago

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.

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6.

MaBaBah:  839 days ago

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.

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7.

kgb:  839 days ago

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...

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8.

arte help:  839 days ago

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

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9.

jerry:  839 days ago

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.

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10.

pinky:  839 days ago

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

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11.

Professor Obvious:  839 days ago

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.

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12.

jeezlouise:  839 days ago

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

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13.

Carl:  839 days ago

Hey Tkennedy,

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

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14.

ginko:  839 days ago

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

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15.

JT:  839 days ago

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

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