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Billy Baldwin on Gossip Girl and Underage Barbados Trips with Mick Jagger

Most middle-aged actors would be flattered to find out that one of the hippest series on television had customized a part for them, but for Billy Baldwin, it was a hard pill to swallow. Baldwin begins his Gossip Girl arc tonight as William van der Woodsen, the long-lost father of Blake Lively's affluent Upper East Sider, but at 46, the second-youngest of the Baldwin brothers had a hard time accepting that he was old enough to play the father of a high-school graduate. In anticipation of his debut, Baldwin talked to Lindsey DiMattina (of our sister site Hollywood Life) about finally embracing his role, his "Jewish geography" conversations with Blake Lively, and his own run-in with privileged Upper East Siders.

How do you feel about playing Blake's dad?

I have a five-year-old daughter, but all my friends from college have children the same age as Serena. They are all going to scout colleges and getting ready for orientations. I certainly am old enough to be Serena or Blake's father, [but] it doesn't make it any easier to take. It wasn't long ago that I would have been -- not the guy with Blake Lively or with Serena, but I was the guy who was with the girl. I wasn't carted off to pasture as grandpa. If you're going to be a father, it's cool to be on a hip show and a show that's so relevant. You know how Bret Favre's teammates make fun of him because he's so old and also his daughter had a child two weeks ago? He's an NFL quarterback and a grandfather. I haven't gotten any of the Brett Favre treatment yet, which is nice.

Have you given Blake any fatherly advice about her love life?

No, not at all. We have lovely little chats on the set about the characters and the work and a little bit of what I call Jewish geography -- where are you from, where did you grow up, how many brothers and sisters -- but I don't get into any of that. Her television father will not be walking down the aisle with whomever her real-life husband winds up being. Lucky young man, I might say.

What was the cast interaction like between the two age groups?

I didn't have a lot of stuff with the younger cast. It was mostly with Connor [Paolo] and Blake and Kelly [Rutherford] and Matt [Settle]. There was a couple of bigger scenes where we had a hundred extras and the other cast members were there. I saw them in hair and makeup. I got to overlap a couple times on the set -- like I arrived a couple of times when Leighton [Meester] was leaving. It wasn't any real opportunity to get close or become good friends. Certainly that happened with Matt and Kelly and with Blake.

Are you guys still in touch now that the filming is over?

I have run into Matt on the streets of New York when I was there. I have also texted and spoken with Kelly a few times. Blake is down in New Orleans working on a film [Green Lantern]. She got cast in one of those big monster action films -- based on a comic book character, one of those $100 million studio spectacles.

Do you think the privileged roles you played on Gossip Girl and Dirty Sexy Money are accurate portrayals of New York's upper class?

Certainly it was heightened on Dirty Sexy Money. You have to have the dramatic act-out, the cliffhanger or season-ending cliff hanger to elevate it a bit. I have friends that grew up in Manhattan and were privileged and went to the Carlyle. I have one friend who was hanging out in Studio 54 with Halston and Calvin Klein -- her mother would take her there when she was 11 and 12 years old. She would go to these places and people would offer her cocaine. She was snorting coke in Studio 54 when she was 12. I say it's heightened and it is, but you would be surprised how accurate and honest and these shows can be based on my experience in them.

My own wife's father divorced her mother when [my wife] was two years old. Her father was John Phillips and then her mom went on to live with Warren Beatty for four years. Then she lived with Jack Nicholson for 3 years, then married Dennis Hopper for a week or two. In the midst of this, she was having an ongoing friendship and relationship with Mick Jagger. My dad was my little league coach and my Cub Master. My wife, when I was at Cub Scouts with my dad, was on private jet with Mick Jagger heading to Barbados when she was 7.

How has your life prepared you for these roles of privileged individuals?

Only my acting has prepared me for this -- certainly not my early life. I grew up as one of six kids. My dad was a high school teacher and made no money. We lived a very modest life -- a lower middle class [life], not destitute, but it was real tough blue collar lower middle class -- but it was a rowdy, rambunctious Irish upbringing.

In my adult life, I started to meet people from different walks of life. I portrayed Robert Chambers, who was the preppy murderer. I had a lot of exposure to privilege on the Upper East Side. When you become famous, you start getting invites to parties where there are famous athletes and famous rock stars, politicians, people who have tremendous power and affluence. It's not in my DNA, but certainly I have been exposed to it.