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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?

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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since there is a longstanding embargo prohibiting American citizens from going to Cuba-guess this is the only way they can pick up their cigars
by doing the "journalist" thing!

has Penn even attended anything other than high school-not sure if he finished that even

Vanity Fair--if you want to send someone to Cuba at least send someone with a degree! and not a left-winger but an objective individual (not leaning right or left) if you want me to read the article

oh-wait a minute-I almost forgot-this has nothing to do with journalism and everything to do with magazine sales

1770 days ago


Vanity Fair's judgment has been questionable since Tina Brown left, imho. But Sean's just crazy enough to make me curious. I'll read it.

1770 days ago


Obama declares "H1N1 a National Emergency"....... yet his daughters have not been vaccinated.


1770 days ago

who dat    

He probably banged her on the way over.

1770 days ago


Birds of the feather do flock together.

1770 days ago


Sean should have spent more time in trying to save his too soon deceased brother alive, instead of Chavez and Castro's regimes. If Sean would have quit smoking, I'm sure little brother Chris would have too---instead Chris dies of a sudden heart attack, and Sean keeps his sights set on wanting to be a Communist.

No wonder his father was Blacklisted---or was he a Snitch? I forgot, but Sean's one of those hate your country, but live it up in Vegas, and never serve your country types.

Have a nice Mile High Flight you two. Barclays Bank is run by Communists.

1770 days ago


I consider myself a good democrat and liberal, but Jane Fonda and this nut job seriously give the all Dem's a bad name and should seriously move out of the country.

1770 days ago

Glory Bee    

Penn Credo : The enemy of my country is my friend. He should go back to Madonna, they really are a good match.

1770 days ago

benny b    

Things are really changing in this country... we latinos are no longer satisfied with living in the shadows as outcasts... working for meager salaries... that is really changing... for example... me and my brother command IT salaries of 60K and 80k respectively as 1st generation immigrants... Latinos throughout the states have begun to realize that the main way to have a 'real' voice in this country is with a leveling and parity of our income purchasing power with those of the anglo majority... we still have a long way to go but we are reducing that gap one day at a time... sooner than later 19th century minded individuals such as bob griese will see their jobs go to latinos and other minorities...

Read more:

1770 days ago


It's "journalism" like Penn's article that made me NOT renew my subscription to Vanity Fair! Their conservative bashing makes me sick, and decided that I could vote with my dollars!

1770 days ago

homie 1 kanobe    

Sean,All I can say is "Keep Dancing In The Mine Field"

1770 days ago


Remember Fast Times at Ridgemont High? "What in the hell do you think you're doing?" and Spicoli says "Learning about Cuba. Having some food" lmao! I guess he really WAS learning about Cuba!

1770 days ago

sarah curran    

Vanity Fair has to be kidding-that crazy left wing head graydon carter wants a story on cuba by sean penn-can you picture the meeting were this one was pitched??? so crazy that maybe they are hoping publicity generates sales. So these socialist dems think this is what americans are interested in-once again only the wealthy need apply-a private jet with the wife of the head of barclays-and cuban travel and spending us dollars is restricted. special treatment again. so they want us all to pay more and suffer but these socialists get to roll in a different manner with a different set of rules. A Vanity Fair boycott is in order. Down with Graydon and all his Obama A** kissing.

1770 days ago


22. I consider myself a good democrat and liberal, but Jane Fonda and this nut job seriously give the all Dem's a bad name and should seriously move out of the country.

Posted at 2:26PM on Oct 25th 2009 by vetter

Same here, I agree.

1770 days ago

mickey lou    

Please stay in Cubaforever!

1770 days ago
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