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Sean Penn -- Sometimes a Cigar...

Posted Oct 25th 2009 12:41PM 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?

Sean Penn -- Sometimes a Cigar...
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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Tags: cuba, fidel castro, FidelCastro, havana, sean penn, SeanPenn

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

Posted at 12:50PM on Oct 25th 2009 by Carl

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

Posted at 12:52PM on Oct 25th 2009 by pizza

3. 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!

Posted at 12:52PM on Oct 25th 2009 by Thomas

4. HE JUST NEEDS SOME ANGER MANAGEMENT.

Posted at 12:55PM on Oct 25th 2009 by HE IS A FINE ACTOR

5. 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.

Posted at 12:59PM on Oct 25th 2009 by TheTruth

6. 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.

Posted at 2:16PM on Oct 25th 2009 by MaBaBah

7. 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...

Posted at 1:06PM on Oct 25th 2009 by kgbmomma

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

Posted at 1:07PM on Oct 25th 2009 by tkennedy

9. 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.

Posted at 1:12PM on Oct 25th 2009 by Jerry

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

Posted at 1:19PM on Oct 25th 2009 by why

11. 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.

Posted at 1:20PM on Oct 25th 2009 by Ditto Head

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

Posted at 1:27PM on Oct 25th 2009 by sandy

13. Hey Tkennedy,

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

Posted at 1:37PM on Oct 25th 2009 by Carl

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

Posted at 1:47PM on Oct 25th 2009 by supp

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

Posted at 1:48PM on Oct 25th 2009 by Hmm

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