There doesn’t seem to be a shortage of music video directors out there who takes a stab at feature films at one point or another. Francis Lawrence, Joseph Kahn, Jonathan Glazer, Tarsem, Mark Romanek, Michel Gondry, and countless others have gone down the feature route, sometimes even managing to invigorate the film world with their palatable efforts. Now all eyes are on Marc Webb.

(500) Days of Summer defiantly questions romantic comedy conventions. Do stars miraculously align even in the most unseasonable moments? Not on Webb’s watch. This is a story about a boy who falls in love with a girl who doesn’t believe in love. The film doesn’t set out to celebrate the genre for its annoying redundancies, the fluff, or the happily ever afters—the film brims with biting self-awareness and leaps over major conventional pitfalls with laudable dexterity.

Anthem ensconced at the Casa del Mar hotel earlier this month to pick Webb’s brain about his past, present and pending future in music videos and feature films. But before you read on, give us a shout at kee@anthemmagazine.com for your chance to score a goody bag from Fox Searchlight Pictures! Tell us, what is the best pickup line you’ve ever heard?

How did you get your start in music videos?

I was an editor for a long time. I worked for a documentary filmmaker named Doug Pray who directed Hype, Scratch, and Infamy. He taught me how to edit. I started editing little things at a record label. That’s when I realized, “Hey, I could make this stuff.” I offered to do some really low budget stuff and gradually, over the course of a couple years, got more and more opportunities and started doing videos fulltime. That’s the short version of the story.

What’s the most memorable video you’ve directed so far?

The most memorable would be P.O.D.’s “Change the World.” The idea for the video was that we were going to have people holding up the lyrics in different parts of the world. We got to travel around the world for 2 weeks and shoot for a day in Beijing, Sydney, Tokyo, Auckland, Cairo, Johannesburg, Moscow, Berlin, Paris, New York… It was an incredible journey. We did it for not a lot of money. It was amazing. But there are a lot of babies that I like—some videos that I like more than others. It’s hard for me to separate the pleasure I had in making them with the result. I like some of the My Chemical Romance videos. I like Fergie’s video for “Clumsy.” I like the Snow Patrol video and Brand New’s “Sic Transit Gloria.” There’s a Sparta video that I did years ago that I really liked that didn’t really get out there. It had a really well crafted edit. I was working within the pop video world, which is a certain kind of world where certain rules apply. They put certain restrictions on your work, but I always enjoyed that.

What are some of those restrictions?

You have to highlight the artist. The artist has to come out looking good. You can’t kill the artist, which is sometimes a bummer. It has to be engaging. If someone’s flipping through the channel, it has to be bright enough. YouTube actually freed people off from this rule, but you’d have to assume that somebody was watching this in a small box in a bright room, which is very different than a movie. With movies, you can go much darker and have much richer palettes in terms of your contrast ratios and stuff. Since music videos are this little thing, you’re competing with someone talking over here and you just have to be like, “Look at me!” It has to be really striking. These rules are always stated implicitly. You want to be “pop-y” and then you get to interpret what that actually means. It means different things to different people.

So these are definitely unwritten rules.

Unwritten rules. I learned from DNA, Inc. where I did music videos. There are a lot of people there who’ve done it for a long time. I’d talk to Francis Lawrence who had an office next to mine or Liz Friedlander. We would often have these conversations about convincing record labels that they were getting what they wanted, what they actually wanted, and what you can get away with. Oftentimes, we were punished. There have been videos that I’ve done that were shelved because we didn’t fit those rules and I felt like an asshole. I don’t want some artist to be spending $200,000 and not get what they’re really looking for. I mean, it’s somebody’s career on the line and you’re responsible for that. You have to take that seriously. I think that’s why I got to make more videos than some people because I took that very seriously and made it less about, “I’m going to express my thing.” Although there were videos where I got to do that.

Is there a particular video that you wrote on and really wanted to get, but didn’t?

Oh, god. There’s so many I can’t even think about it. I wrote on a Rolling Stones video one time and I really wanted it to happen. There was… oh, boy. [Laughs] Too many. I was often rejected and still am.

Do you see and/or experience the things that other video directors constantly howl about—falling budgets, restrictions on creative freedom, record labels unwilling to take risks—even though you’re one of the top-tier directors in the industry?

Absolutely. There was a panic period a couple of years ago where the video commissioners had less control. All the high level executives who ran the music video departments got fired because their salaries were too high. So there were a lot of junior executives who didn’t have as much influence or experience handling the videos. There was a lot of waste. Bands who had been steeped in making very expensive videos and used to a certain sort of luxury and capability no longer had that. I think there was a clampdown, which made record labels go, “You have to do this and you can’t mess around at all” because it was a reaction to the mismanagement of that division. It makes sense what happened because the revenues for music videos were just killed. They’re usually pretty cool though. It just depends on the band to be honest with you, in terms of creative freedom and flexibility. I always thought that if you work on a low-budget job you have a little more leeway. I haven’t done a lot of videos in the last couple of years because I was doing a movie, but it’s probably still true to a certain degree. I just did a Green Day video last week and they were great. I dealt with the band and somebody at the label—they don’t fuck around with you.

Is it your ultimate goal to make a transition into directing feature films fulltime?

I don’t think I’ll ever leave music videos as long as music videos exist. They tend to be smaller [nowadays], but there are still a lot of them happening. I love music videos. I think it’s a really fun format and it’s evolving. It’s a very dynamic art form. In a way, it’s a lot like it was in the early 90s now, which means that they’re making a lot of videos, but they’re not spending a lot of money on them because of Youtube and such. For me, I didn’t have MTV when I was growing up so it was never on my agenda to do music videos. But when I came out here, it was the only way that I could get a chance to direct stuff. I always wanted to do movies.

How did the (500) Days of Summer screenplay fall into your lap?

Fall into my lap… There was just a pile of them—it was so easy! [Laughs] Mason Novick, one of the producers of the movie, gave it to me. He gave me a couple of scripts and said, “This one is set up at a studio. It’s about a magician. You’re going to hate it. There’s this one, (500) Days of Summer. It’s kind of a romantic comedy. You’re probably going to like it, but no one wants to make it.” I didn’t want to do a romantic comedy, but I read it and it felt different enough that I could relate to it, you know? We spent the next six months trying to convince people that I could do it and then spent another year developing the material, casting it, and eventually shooting it.

Would you say this is a rebuttal on romantic comedies?

That’s interesting. Somebody actually just described it as being “an emotional action movie,” which I kind of like. It’s definitely a pop movie. It uses these genre set pieces that a lot of romantic comedies do, but it arrives at them in a different way and conclusion. I think rebuttal is a good term for that. I don’t think it’s a cynical movie, but it’s a little bit more honest. I always thought of it as being a coming of age story masquerading as a romantic comedy.

Since you’re not so much into romantic comedies, what genre would you most like to work in?

I don’t have a favorite genre, but I’ll tell you that I like directors who jump genres like Alfonso Cuarón. He doesn’t make the same movie twice and that I really admire. I want to do something more action-driven, a little bit more “testosterone-y” next. I like certain kinds of horror movies like The Orphanage. I don’t know if you saw that.

I actually saw that twice in the theaters.

That was fucking awesome. The horror genre I think is a real testing ground for directors. It’s about technique and creating a world’s atmosphere. That’s how to really scare people. It’s the power of filmmaking in a very visceral box. I find that appealing. But, I don’t want to think too much about it. I just want to do what moves me or find something that’s interesting. I don’t want to repeat myself. I don’t think you’ll find me making romantic comedies anytime soon.

Let’s journey back to (500) Days of Summer. How did you end up casting Joseph Gordon-Levitt and Zooey Deschanel for the film?

I met Joe a couple of years ago and we had a talk about the script. He just got it. There’s ways to cast this with a goofier funnyman, but because there is so much whimsy in the script, if you cast a comedian or someone who’s going for the joke, you lose the core of it. I wanted an actor who I could rely on and he’s just great. As for Zooey, she was the perfect girl for this. She’s so likeable. I think that character is a tricky character to make likeable or at least relatable and she did a great job with that. The other thing is, you can’t cast a movie like this in an arbitrary way. You have to think about their dynamic and whether they fit together. They had done this movie together called Manic in 2000, I believe. I watched it and there was something there. They had known each other so there was a built in familiarity between the two of them. I think some actors can fake it, but we had a lot to build on, which was great.

Do Joe and Zooey like to work a certain way?

They work very differently. With Joe, we sat down and went over the script for 3 – 4 weeks before we started shooting. We talked about the architecture of the scenes, how we were going to block it, and really got deep into it, which is a great process because I can sort of think about it and it was a meeting of the minds. We knew where we were both going. Zooey doesn’t like to rehearse. She likes to discover things in the moment. We rehearsed a little bit so we knew where we were heading in general terms, but she didn’t want to give it all up and try to repeat something. She said, “We have to keep it alive.” She takes a couple of takes on set to warm up and she’ll constantly be finding new things, which is fantastic. There are so many moments in the movie that she invented. There’s a scene that takes place in the copy room where she goes into kiss him. She walks away and then comes back to look at him and then leaves. That’s all Zooey. It makes that scene work whereas it won’t work without that. She only does what’s honest; she won’t fake it. Joe’s like, first two takes and he’s got it. Sometimes it was tricky to give them some overlap, but ultimately, they’re good friends and such pros that it was totally easy to deal with. They made my job pretty smooth. It’s like when they say that 85% of directing is casting. I’d say it’s more like 70%, but still…

Did you find it jarring directing a narrative-driven feature with actors coming from a background in videos?

It was actually easier, honestly. Music videos are a little bit from the hip. You have less money… well, that’s not true, but you’re under the gun a lot more. It was a smoother thing. You’re telling a story and you’re relating to it as a human rather than it happening in front of your eyes and relying on the editing. In a way it was easier to track the emotion of it. There are certain surprises in terms of the personnel. I never had a camera operator before and I communicated a lot with the camera operator on set. I had done so many music videos that I knew the nuts and bolts well enough that it didn’t pile up and really freak me out. So much of directing is fucking stupid little decision making like, “What color should the walls be?” and “Why is he wearing these shoes and not those shoes?” As long as you have some mechanism to help you with those decisions so they’re not arbitrary, you’re in a much better spot.

How involved were you in putting together the soundtrack for the film and do the songs speak to your own musical tastes?

I had total control over that, but within what we could afford. I really like the soundtrack, but is it my own musical tastes? The music has to fit within a certain genre and tone. I like some heavy thrash metal stuff like Boris, All That Jazz, and musicals a lot. I don’t listen to The Smiths all the time, but Scott [Neustadter] really likes The Smiths and that’s why he wrote it into the movie. I definitely like the music and have an emotional connection to it. It’s somewhat reflective of my musical tastes, but it’s a small segment of it. A lot of the music I run into is from doing music videos. I’ve done music videos with Regina Spektor and I’ve written some treatments for Wolfmother. Andrea Von Foerster and Amy Driscoll brought in a couple of songs like The Black Lips. Sweet Disposition was something that Amy brought in from Fox Searchlight because they were unsigned at the time and it just worked. We wanted to use “Please, Please, Please” by The Smiths song there, but we couldn’t afford multiple uses. We had to find some analogous tonal piece to substitute for that.

I’m sure you’ve been asked this question a million times already, but I’m going to be one of those annoying journalists. Who is Jenny Beckman?

Who’s Jenny Beckman? You’re actually the only person who got the name right. She’s on Facebook. Do you want me to show you?

Sure. Is this someone from your past?

We’ve all been Jenny Beckman or you’ve known Jenny Beckman. This movie was sort of an amalgam of a few different girls. It all started out with Scott’s experience, and we all drew a little bit of our war stories in there. You’ll have to ask Scott about that. She’s… [Laughs] I don’t know what we’re legally allowed to say.

Well, it was a great start to the movie because it gets that first laugh.

You’re right. It’s funny and it lets you know that it’s not going to be your typical kind of a movie. It makes you say, “Okay, I might have to read. I’m gonna have to pay attention.” But the other tricky part is that the first part of the movie is very pop, it’s supposed to be in a certain genre. We wanted to make it easy at the start and that line upfront let’s you know that you can expect something different. It sort of cleanses the palette.

What are you working on next?

There are a few projects that I’m trying to line up. Scott and Michael [Weber] just wrote an adaptation for a book called “The Spectacular Now,” which we’re working on. There are a couple of novels… I really want to tell you, but I can’t talk about it because the deal’s not done. There’s a musical that I want to do. There are a couple of other things. Nothing is locked and ready to go.

So, you’re definitely going down the feature route.

Oh yeah. I’ll still do music videos hopefully as long as they’ll have me and they actually make them, but I definitely want to make movies.

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