When we began our interview, I asked Matt Weiner, “So all those Emmys aren’t good enough? You’re going for the Oscar now?” He laughed and said, “I don’t expect  to enter at that level but I’m getting to make something really important to me. So I’m really excited.” As previously reported, the multiple Emmy winner (7 for Mad Men and 2 for The Sopranos) who created AMC’s much-lauded Mad Men is using his down time from the show to jump into the perilous waters of indie filmmaking as director and writer of a longtime pet project, You Are Here. Now in its fifth season, Weiner only finished up the new season of Mad Men two weeks ago but has already arrived in North Carolina this week to begin pre-production and expects to start the two-month shoot on May 7th. The comedy stars Owen Wilson, Zach Galifianakis and Amy Poehler in a story of two childhood best friends who embark on a road trip home after one of them discovers his estranged father has died.

Weiner has been trying to launch You Are Here for 8 years, “I’ve re-written it a few times, I haven’t been available for part of the time, and the rest of it is just how hard it is to get a movie made. Especially an adult movie, one that doesn’t have a high concept, ” he says. “I tried to get it together during other off-seasons and just hadn’t been able to get the right casting or financing. It’s like, you get the cast and you can get the financing, but sometimes you can’t get the cast unless you have the financing and there’s all the stuff about foreign sales. It’s a lot more producing than I thought I would have to do. But we found somebody amazing who has wanted to make the movie for a long time. So it was perfect timing.”

The person he refers to is Gary Gilbert whose Gilbert Films has been behind indie hits like The Kids Are All Right and Garden State. Gilbert backed Kenneth Lonergan’s Margaret which was stuck in legal limbo for five years before getting a nominal release last year from Fox Searchlight. Lionsgate, which produces Mad Men, is on board to handle international sales. But there is no domestic distributor lined up. Although Weiner’s previous deal allowed for him to do a film for Lionsgate, You Are Here won’t be it.

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Some might be surprised his first feature is a comedy. But, although Weiner is known for his dramatic TV series, he has worked in sitcoms before, most notably at Ted Danson’s Becker. “This film has a tough genre. The most notable quality to it is that it’s funny. And I always think that funny is the best environment to tell a serious story. You know, believe it or not, there’s a lot of humor in Mad Men. Especially in the dark moments. So I felt that I wanted to write a movie about friendship, and male friendship in particular, and the mystery of friendship that holds people together.”

Although Weiner has directed several episodes of Mad Men, it’s not always easy to convince financiers to go with a first-time feature director. But Weiner felt the story was too personal to consider anyone else to helm it. “It was a problem at the beginning. They were like, ‘We can sell this script, but you’re not going to direct it.’  But I wrote it between my first and seconds seasons on The Sopranos and I thought here is my chance to at least try to make my way into feature directing. I really thought it would come faster than this.”

As for casting, Weiner tells me he wanted Owen Wilson “to be this guy from the beginning. I’m a huge Bottle Rocket fan, and I’ve always thought he has a unique presence. It took me a long time to get it to him.” As for Galifianakis, Weiner says the comic actor wasn’t high profile when the script was initially written. But about four or five years ago, his Mad Men star Jon Hamm told Weiner he knew Galifianakis was the right guy for it. And that was right before The Hangover. Weiner talked to him about it, but it was hard to get a committment for a movie that didn’t really exist with any financing at that point.

After Weiner finishes the film around July 4th, he expects to dive right back into the 12-week writing session for Mad Men’s 6th season and simultaneously edit the film. He wants to have it ready by January 2013 perhaps in time for Sundance or even Cannes. Among those Mad Men alumni working with him on the film are producer Scott Hornbacher, cinematographer Chris Manley,  production designer Dan Bishop and Emmy-winning casting directors  Carrie Audino and Laura Schiff.

Meanwhile, Weiner tells me he’s extremely pleased with the public reaction to the new season of Mad Men, which was delayed due to contract negotiations and spent 17 months off the air. It returned to its highest ratings ever and generally good reviews, setting it up for a run at a possible unprecedented 5th consecutive Best Drama Series Emmy. Weiner didn’t wish to speculate on that but did say the final 3 episodes of this season are the best in the series’ history. He’s not really too perturbed even by a negative review from The New York Times. “We had an incident last year with them spoiling the show. All I know is I read The New York Times and I can never tell what Alessandra Stanley is writing about. We’ve gotten good reviews that I couldn’t tell were good, and I couldn’t tell this was bad so [laughs] I am glad they are talking about it. That’s all I really care about. And I’m glad people have embraced it because there’s a huge anxiety about being off the air that long.”.

The plan he says is to wind up the series after Season 7. “It would give us 85 episodes. I think there were 88 Sopranos,” he says. He finds it encouraging that many TV people, including Sopranos creator David Chase who has a new film coming out this Fall, are moving smoothly into doing independent movies now. It seems like a natural progression considering the edgy and acclaimed kind of TV these creators do. “I feel like it’s worth taking a chance on the people who are delivering this particular kind of entertainment right now.  We are all used to working on a budget. My season cost less than your average Hollywood movie – and it’s 13 hours! I think my movie is going to be about half of what The Descendants cost. It’s 110 pages so why wouldn’t it cost the same as two Mad Men [episodes]? But it doesn’t. It costs more,” he says.

But bottom line, at any price, this is the moment Matt Weiner has been waiting for. “It’s gratifying to me to be finally rolling this film because, whatever success there has been for me in television and for which I am extremely grateful, it did not make this any easier. And I think that it’s always about the material. I would never hope for another Mad Men, but I’m glad I’ve found somebody who believes in it the way AMC believes in Mad Men.”