TMZ

Our TV Shows

Got a Tip?

Call TMZ at (888) 847-9869 or Click Here

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?

0921-media-removed-michael-jackson
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

No Avatar
46.

chicken head    

LOOSER!!!!!!!!!!!!!!!!!!!!

PS CUBA HATES QUEERS!!!
ASK THEIR LEADERS WHAT THEY DO TO THEM!
but here if we say we don't care for their lifestyle
we are called bigots by Sean Penns people and F ing Hollywood and TMZ!

1763 days ago
47.

Mike    

Mr Penn will undoubtedly give the usual Hollywood report on Cuba. Along with Harry Belafante, Oliver Stone and Ted Turner who all praise Cuba. He will give a pro propaganda report like Michael Moores' "Sicko, which conveniently forgot to to tell his audience, the hospital he visits in the movie is for TOURISTS only, no Cuban citizens allowed. Cuba is a horrible place. No freedom of thought, freedom of press, freedom of expression. A recent You tube video called "Panfilo", in which a man interrupts the interview to claim they need FOOD in Cuba, garnered the man two years in prison. No one risks their lives on a raft in dangerous seas, to flee a place unless they are desperate. Report on that Mr Penn.

1763 days ago
48.

janalal4    

He looks like he's just waiting for someone to come close to him so he can whack 'em!

1763 days ago
49.

Foody    

Hollywood so thinks that they are the moral compass and justice fighters for the world. BAH! DELUSIONAL MUCH!!!

1763 days ago
50.

causeiamok    

AND HE SHOULD SHOULD STAY THERE. AND EVERYONE ELSE THAT AGREES WITH SOCIALISM SHOULD LEAVE THE COUNTRY AS WELL. THEN TELL ME IF YOU THINK THESE COUNTRIES ARE BETTER OFF THAN AMERICA. DO YOU REALLY WANT THE GOVERNMENT INVOLVED AND RUNNING EVERY ASPECT OF YOUR LIFE? WAKE UP PEOPLE. GET INVOLVED. DO YOUR RESEARCH.

1763 days ago
51.

Sharona    

I do not understand how Sean Penn is allowed to visit Cuba. I have dual citizenship, as my Dad is an Aussie and my Mom, American.

Cuba is very beautiful. The gun-toting soldiers patrolling the beaches and the streets - not so much. I love NYC and Australia equally. Cuba -not so much!

1763 days ago
52.

He's just another Idiot    

Sean is such a NUTCASE. Bet his wife is glad to be rid of him. Also, he is so UGLY. So, he didn't graduate from High School? That explains a lot of things. Why do these uneducated Hollywood types think they know it all? But the Prize for the biggest Ego in America goes to Obama. I can't stand to watch him strutting around on TV all the time. So far, the only talent Obama seems to have is reading a teleprompter.

1763 days ago
53.

He's just another Idiot    

I agree wirh you #58. All Politicians (and I have known many of them) are supreme Narcisists with enormous egos. However, Obama is the Champ. I don't recall any President in History who is more in love with himself as Obama. Where did that come from? He was raised by his Grandparents and I'm sure they didn't raise him to believe he is God's Gift to the World. His swagger and the way he speaks reminds me of a Tin Horn Dictator. I hope America survives the next three years. I know he won't have a second term so maybe that's why he is trying to destroy us as soon as he can.

1763 days ago
54.

blueangel    

He's no journalist so why is he really going to Cuba?? Most likely to bring back drugs. This guy is a piece of crap. He should just stay in Cuba.

1763 days ago
55.

Mikey    

Jeff Spicoli - eatin some food and learnin about Cuba............

1763 days ago
56.

Mikey    

Who's he going to interview, Fidel "Weekend at Bernies" Castro?!

1763 days ago
57.

progamer97    

off to smoke fidel's cigar.

1763 days ago
58.

penny green    

Where is his buddies Stone and Glover, and yes that bitch Fonda, Wish all of them would fly to Cuba and never be allowed back on America soil, bunch of commie traitors

1763 days ago
59.

kevin    

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

Right-Wing nut jobs suck. But so do left-wing nutjobs like Penn.

1763 days ago
60.

Mary    

Why doesn't he just stay in Cuba, then go hang out with Chavez and Oliver StoneD. It must be nice to be a multi-millionaire liberal. You have all the answers, all the money, but instead of founding a charity, you have to promote the Obama agenda. If Obama really knew what in the hell he was doing, I don't think he'd need the help of his liberal Hollywood crowd. Obviously things aren't going as planned...and that's good for America.

1763 days ago
Previous 15 Comments | 1 | 2 | 3 | 4 | 5 | Most Recent | Next 15 Comments

Around The Web