Sam Jones excels at mostly everything he does—except staying static.

“I just could not sit around on an afternoon and smoke pot and watch TV—that was just never gonna be me.”

With every new project he takes on, Sam approaches it with a skateboarder’s mentality, dating back to his days growing up in Fullerton, California. That do-it-yourself mindset has taken Sam down many paths, including director, photographer and now host of his very one show Off Camera, in which he speaks to a wide range of subjects with the genuine curiosity of a fan and experience of a peer.

With a resume that includes covers of Vanity Fair, Esquire and GQ—and not to mention my personal favorite album cover for Wilco’s classic Yankee Hotel Foxtrot—Sam constantly pushes himself to explore new territories. Whether he’s following Wilco around with a camera, flying with Barack Obama on the campaign trail or talking to Nick Kroll about sketch comedy, Sam’s authentic approach to his work is truly inspiring.

I got a chance to talk with Sam about photography, hanging out with President Obama and the art of the conversation.

Since I started interviewing different artists, one thing that has come up quite often is a background in skateboarding, which you also have. What is it about skating that lends itself to creativity?

Most artists at some point look around and go, “There’s gotta be more to do than this.” And that’s sort of how I started. I was always trying to amuse myself and do fun things and I was never really satisfied with the things that seemed to make other people happy. I just could not sit around on an afternoon and smoke pot and watch TV—that was just never gonna be me. I was always pretty active and made things and skateboarding was just one of those things that really hit a lot of curves for me. There’s the aspect of camaraderie with the other people who enjoy it and then there’s the creative aspect of finding a place to skate or building a ramp. Then there’s the artwork associated with skating—plus it’s a really great photography subject. So, I think it’s just based around trying to have this exciting life.

Well your photography is mostly focused around portraiture. Coming from that background, how do you think the idea of a capturing someone through a portrait has translated into the type of profiles you do on your show?

Well, when you make a portrait of somebody, there’s an attempt to portray them. The very idea of a portrait is an attempt to understand more about who we are as human beings by looking at someone in a certain way or through a certain light. And of course, with photography, you can add so much to a portrait—in terms of storytelling. So, I think that for me, it was the kind of photography where I was never going to repeat myself, because every time you photograph someone, it’s a new experience—it’s a new subject. Even to some extent with skateboarding or music photography, there’s maybe more constraints on what you can do. With portraits, it’s pretty much this idea that anything goes. Any idea that I have or any idea I want to try is possible with a portrait. I was drawn to that because I can explore things artistically and creatively and I can also get to know somebody in a way that by reflecting the things I found out about that person into the art, I can make something that hopefully satisfies my urges of authenticity. It’s as simple as this: You probably know your father better than anybody. So how do you make a picture of your father and what kinds of things go into that picture? I think I’m just very attracted to finding out what makes people motivated and what makes them who they are and a portrait session is a great way to explore that. Off Camera grew from that idea as a more complex portrait, really.

I’ve noticed your portraits are sort of split into two categories. A lot of them have this illustrative, scenic quality, while others are more simple, straightforward portraits. How are you able to make the distinction of which subject fits into one format over the other?

There’s multiple ways to approach a portrait with anybody. For me, I’m trying multiple ideas because I usually don’t know what the best approach is going to be until I meet the person. Sometimes I’ll get to the shoot and I’ll have this whole elaborate idea planned that I think might illustrate this person really well, and after we do all that, I’ll end up making some really simple portrait. Sometimes, for one reason or another, that simple portrait might be what ends up speaking to me and the subject much more than some elaborate idea. Oftentimes it’s an editing process, in terms of finding the image that seems to work the best. And that changes, based on my interests, too. There may be times when I want to do something really cinematic and then there are times where I want to see if I can get a whole piece of expression into one simple portrait. What I always say about my pictures is that I’m not somebody who’s going to take the subject and fit them into my world. I’m gonna go out there and meet them and hopefully be open enough to let the picture reflect who they actually are, rather than make them into a character.

It seems like you spend a lot of time getting to know your subjects, which ultimately influences the outcome of the photo. But obviously for certain subjects, you’re not gonna get two hours to talk before a shoot. Do you think a lack of personal connection affects your photos?

I’m always trying to make a connection, just ‘cause that’s who I am as a person. But, I think that tends to get overstated a bit. It’s often a desire to tell someone’s publicist you’d like to have a phone call with the subject beforehand or to have a long conversation once you get to set. But the truth is that often doesn’t happen. It’s more like, you’re really gonna connect with certain people and some people you’re not. Sometimes you’re gonna have 30 minutes and sometimes you’re gonna have six hours. Every situation is different, but I believe that if I’m myself and I’m genuinely curious in that person—no matter what the circumstances—those things that I bring will help that portrait, in that sense.

I imagine that must’ve been the case when you shot Barack Obama for Rolling Stone. What was the process like, getting Obama while he was still just running for President and likely not having all the time in the world to capture those images?

The funny thing about that whole thing is that I was actually traveling around with him for five days. The idea was that I’d travel around him and shoot reportage and environmental portrait stuff and at one point he’d stop and sit for a cover. So, at one point, we were flying around in the press plane and he was incredibly kind. I remember the Dodgers were in the playoffs with the Cubs and throughout he week the series was tied. And one day he brought back these brownies his mother had made and we sat around and just talked about baseball and stuff. But, his schedule was sorta coordinated by his advance team and I remember one stop where he was setup to do the portrait, but he had to go and do some emergency vote in Congress, so that got scrapped. And at a certain point, I was on that job longer than I’d hoped and I was away from my wife and kids, so I was just looking for somewhere to get the photo taken, and his team eventually found me 30 minutes on a stop. So, we didn’t have as much time with the photo-shoot itself, but that back-and-forth about the NLDS helped out. But I like that picture because I feel like it really shows who he is. I didn’t try to make him super handsome or super presidential, I just shot it how I’d shoot anybody else. I like that picture because it feels really human to me. On that same trip, I took a picture in the front of the plane of him reading a newspaper, and that looked very presidential to me. But that portrait on the cover felt really human to me. That was the difference for me age-wise and who he was as a person and how quickly he ascended to being a front-runner in the race. He was just so much more approachable, it seemed, than other Presidents. Maybe that was just how close we were in age or from spending time with him, but I wanted to reflect that in the portrait.

Well, with Off Camera, you have the luxury of being able to speak for a lengthy period, which must have a pretty big impact on the shoot.

Since I started doing Off Camera, I’ve had the advantage of having this very long conversation before we take the pictures. That really creates a lot of intimacy and a lot of collaboration because we’ve just spent two hours working together and talking. So, that’s extremely beneficial. With the show, I make very simple portraits a lot of the time, and I’m sort of counting that relationship that’s just happened in the room for a couple hours as bringing something extra. Often, the thing that you’re talking about—when it’s not there—feels more like a pose or it feels more like there’s less depth in the expression. Sometimes that might be good, but what you’re really looking for is access to someone letting their guard down, being themselves and not having an agenda of how to pose. You can just be a human with another human, and Off Camera—by nature of just how we film the conversation first—makes it pretty easy to have that relaxed vibe.

That’s something that really drew me to your show. There are podcasts where people are able to talk about a wide range of topics, but you don’t really see too many TV shows where you get any more than 10 minutes to talk, and it’s usually promoting something. What was the basis for the type of conversations you wanted to bring to your show?

Well, we have a much longer time than The Tonight Show, or whatever, and we have a different agenda. We’re not trying to be entertaining as the first order of business. We’re not trying to get seven minutes of great entertainment that’ll keep people from changing the channel. So, we have the ability that if I get interested in a topic with someone, then I can explore that for 45 minutes and still have twice as much time as somebody on The Tonight Show might have to talk about a recent project. But, with every guest it’s different. I try to figure out what I’m most interested in and what kind of conversation I can have with this person, given their background or specific skills or whatever it is. Based on that, I try to just put an outline in my head of where I would like to hopefully get to, but still be open enough to change that if something comes up in the room. And I think that goes back to how I approach a photo-shoot, in that it probably changes with my interests. Sometimes I’m really interested with psychology and the upbringing of these people and sometimes I’m just really curious about the craft or their process.

You do have a ton of variety on the show. One week you’re talking with Tony Hawk about Stacy Peralta and then you’re talking to Lauren Lapkus about improv. Are you just genuinely curious in these different types of creative people?

Absolutely. I could never have been like Michael Jordan—not that I could’ve—because I would’ve gotten totally bored playing basketball all the time. I’d rather play basketball on Tuesday, skate on Wednesday and build a model, see if I could film it to look like Star Wars on Thursday and then go jump off that bridge into the river on Friday. So, I was never the kid who could focus on one thing exclusively and I’m still like that to this day. In general, if you’re watching the show, the people who are coming on to talk are people I’m excited to speak to. There’s a huge number of actors because I can’t just put on all my skateboard heroes. The show would be taken off the air. But, I love talking to actors about acting because I don’t totally understand it, but I direct actors and I’m so curious to know what’s going through their minds. I feel like each actor has such a specific way that they get to their own success that it’s almost like talking to people with different jobs.

In one of your conversations, you talk about people getting pigeonholed into being known for one specific thing. You’re example was Kramer from Seinfeld. How do you think trying out all of these different types of career paths has impacted your work?

It’s probably been more detrimental to me, because I think if I was just a photographer or just a director, it might be easier for me to find work because people could define me. Every time I try something new, I have to climb that hill all over again and meet all the people in that industry, figure out how that works and gain acceptance. But I think the reason I do that is because I enjoy the challenge of it. I will say this about photography: I love doing it and everyday you do a photo-shoot it’s like a new job, but it’s no longer as much of a challenge in terms of having a problem to solve. There’s a certain joy you get when you take something on and you feel like you’ve succeeded at it, that journey is really intoxicating to me. I don’t know how you feel much like an artist if you’re just repeating everything you do. For me, the way to struggle with it is if I go off and make a documentary and it’s incredibly difficult and painful, then photography looks a lot better to come back to. That’s probably part of the strategy, too. When one thing feels too much like I’m on autopilot, a good way to appreciate something is to go off and try something else for a little while.

You mention the struggles with a documentary, and so I wanted to ask you about the Wilco documentary I Am Trying to Break Your Heart. I know you basically initially funded it yourself, but it seems like you were in the right place at the right time, documenting such a turning point in the band’s career. What was that experience like for you?

Well, whatever Jeff [Tweedy] or any of the guys were, that was the work they were making at that time and that was exciting to be around. For me, it was my film school, in a sense. I thought their music was interesting and I thought that the way they conducted themselves in terms of being a real band and not yet having radio success, but being able to pull in some pretty passionate people with that kind of songwriting—all of those elements made them an interesting band in the sense of all the other bands I’d been attracted to growing up. You gotta remember, they were a pretty small band at that point. After I started that project, I’d tell people what I was working on and nine out of 10 people hadn’t heard of them. But, they were pretty close to my age, so my mindset wasn’t that I was around these geniuses making this classic record, it was more like I felt like I was around some hardworking guys who were great songwriters, and it was fun to go on that journey with them. One of the good things about that movie is that I wasn’t some crazy fan that was nervous to be around Jeff or anything. It was a pretty relaxed, casual thing from the start. I just had so much going on with figuring out the story and how to adequately figure out how to film it, that when you’re in the middle of those things you’re kind of just in there with your head down.

Well in the same sense, Off Camera is definitely a departure from anything else you’ve done. One thing I love about the show is how you approach talking to your guests. You refer to it as a conversation, instead of an interview. Why is that?

By nature, I think an interview is like, you come in with a list of questions and the person answers and then you move onto your list of other questions. And we’ve all heard the interview where someone asks a question and the guest responds with this really intriguing response that just begs a follow-up and instead they just jump into some totally different question. A conversation naturally flows through a curiosity and desire for sharing information between two people. And it’s not that Off Camera is a “conversation,” because ultimately I’m always trying to turn the attention back onto the guests. And we’ve had times where they might ask me my opinion or something, but I try to minimize that stuff, because I’m not doing a show so people could tune in and hear all about me. But, it’s more of a conversation than an interview, because I don’t know when they start answering the question what I’m going to ask next. Instead, I’m trying to sit there and listen to them, and then based on whatever they said, I’m trying to make a connection with something that comes up in my mind or that interests me. I’m trying to connect the dots and have a narrative, but I don’t want to force it.

That’s a great point, because when I think of an interview, it reminds me of job interviews where someone has the power, and they’re trying to figure out something about a person that suits their needs. With a conversation, you’re almost on the same level.

Part of a conversation is to share ideas and communicate the feelings about things to each other. So, if I have a feeling about what the research process is like, it’s very easy to relate to that. I can either choose to tell my five minute story about how I relate to that, or I can say, “I relate to that and I sometimes lose myself in it,” and turn the focus back on them. But even doing that in the room, it still feels like a total conversation. To me, I think there’s an opportunity to find a thread or path that you’d never discover if you were going down a list of questions that you just needed answers to. So, I think the difference between an interview and conversation is really the difference between having and not having control. If I really wanted to just get my questions answered, I wouldn’t try to relate or follow-up on anything. If I was just interviewing, I’d just go down my list of questions.

One reason I enjoy these long-form conversations is because I always read profiles where the journalist tends to put their own interpretation onto a subject after spending only a few hours together, which seems kind of unfair. Your show usually has a short monologue describing the person, but for the most part, the subject gets to speak for themselves.

Yeah and the truth is, most people who have been on the other end of that and have had profiles written about them—I think the general response every time a piece comes out is like, “Oh, well it’s not enough to call them and complain, ‘cause then I’m an ass hole, but I can see how they sort of used me in a way that’s more entertaining for their readers.” That’s sort of the general experience, rather than seeing the piece later and being like, “Wow, they really got me.” One reason I don’t like the term “interview” is because it suggests that I’m a journalist and I tell everyone that comes here that I’m not a journalist. I’m not trying to develop a theme or a lead. And I’m not trying to fit their narrative into a thesis I’m trying to prove or be a news source for anybody. I’m simply curious to get to know how they do what they do.

I think that’s what really helps Off Camera stand out from some of these other talk shows. There are so many games and bits on a lot of these shows, but not enough room for actual conversations.

I was watching Jimmy Fallon a couple years ago, and Julia Roberts agreed to let him throw a ball in her face in. And I thought, “It’s fine if we have some shows where you throw a ball at Julia Roberts’ face, but what happens if we don’t have a show where she gets to talk about her craft a little bit and this was the only option?” I think it’s interesting to talk to these people more as craftsman instead of as celebrities. It sort of signifies our boredom with their work if we only have seven minutes with them and throw a ball at them. That’s fine for what it is, but I like the idea that we can be the other extreme of that. The funny thing is, we sit around over here and try to think of other shows that are trying this. I feel like in the ‘70s and ‘80s there were a lot of shows like this, and I miss those shows. It’s not like we reinvented the wheel, but it’s certainly a space nobody else is really taking advantage of.