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Sean Penn is a big Bachelor fan, likes to watch the girls cry

Sean Penn’s reality show guilty pleasure with fiancee Charlize Theron is The Bachelor, though he usually fasts forward through the talking to get to the parts where people cry. “I don’t really want to hear the conversations. I want to know the decisions. Is he gonna decide on this one or this one?” Penn said…

Sean Penn says marriage to Charlize Theron would be his first, two ex-wives likely beg to differ
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Sean Penn says marriage to Charlize Theron would be his first, two ex-wives likely beg to differ

It’s no secret that Sean Penn and Charlize Theron are hot ‘n’ heavy ‘n’ very quickly working toward marriage. And love like that can make a person say and do some crazy things, such as forget he was married twice before. “You say I’ve been married twice before but I’ve been married under circumstances where…

Sean Penn is filing to adopt Charlize Theron’s son
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Sean Penn is filing to adopt Charlize Theron’s son

After more than a year together, Charlize Theron and Sean Penn recently sparked engagement rumors when she was seen out with a ring on that finger. Although there hasn’t been any confirmation about their relationship status, multiple sources say the pair is taking a big step in their relationship — by having Sean adopt Charlize’s…

REPORT Charlize Theron engaged to Sean Penn
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REPORT Charlize Theron engaged to Sean Penn

According to a new report, Charlize Theron and Sean Penn are engaged. Penn, 54, proposed to Theron, 39, during a trip to Paris back in November. A source with Us said they, “decided to take their relationship to the next level.” The Academy Award-winning actors first stepped out together in December 2013. Interestingly enough –…

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VIDEO Sean Penn describes “personal fantasy” about Julia Roberts eating in 3-D

Sean Penn has submitted his name into the fascinatingly strange award presentation clips hall of fame with his dedication speech for actress Julia Roberts at Monday night’s 2013 Hollywood Film Awards. During his rambling in which he started off asking if drinks were free on stage as well, he went on an amazingly awkward ramble about a “personal fantasy” involving watching Julia eat in 3D. We’ve got the clip cued up to the strangeness as well as a transcript during which Penn pines, “How great would it be to sit there watching a Julia Roberts movie, eating in 3D, she’s eating corn on the cob and then something gets stuck here (gestures between his teeth) and you could take your virtual toothpick and say, ‘I got that babe?'” Oh – Julia’s response is priceless too!

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VIDEO Bradley Cooper before he was famous asking on Inside the Actor’s Studio with Sean Penn and Robert De Niro

38-year-old Bradley Cooper is People‘s Sexiest Man Alive, and is enjoying both critical and box office success in The Silver Linings Playbook, but he’s been chasing his dreams for a long time.

When he was 24-years-old Bradley worked as a doorman at the Morgan Hotel while getting his MFA from NYU’s drama school. He would hold the door people like Leonardo DiCaprio, who’s now one of his buddies. He also got the chance to ask Sean Penn a question on a 1999 episode of Inside The Actor’s Studio.

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PHOTO Sad Keanu Reeves and sad Sean Penn in drag

I wasn’t planning on joining in on the sad Keanu Reeves meme and I wasn’t planning on posting any more photos of Sean Penn looking like a brunette Phyllis Diller, but much like the invention of Reese’s Cups, the collision of the two was undeniably awesome.

Hey, you got transvestite Sean Penn in my sad Keanu Reeves!

Oh yeah? Well you got sad Keanu Reeves in my transvestite Sean Penn!

(Together) Mmmmmmm… That’s good!

PHOTOS Sean Penn in hard rock drag for ‘This Must be the Place’

Sean Penn is currently filming The Rocky Horror Picture Show Part 2 This Must be the Place in which he plays Cheyenne, a retired rock star looking for his Jewish father’s killer and nice pair of fishnet stockings. See photos of the nearly transvestabulous Penn in character on the streets of New York City Wednesday!