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That's My Boy's Andy Samberg On Working With Sandler And Why He Doesn't Want To Direct

In the last few years the best part of Saturday Night Live has been the digital shorts made by Andy Samberg, Akiva Schaffer and Jorma Taccone, also known as The Lonely Island. Since the videos started coming out all three members of the group have experienced success, but in different areas. While Samberg has stuck to acting and writing, both Schaffer and Taccone have tested their skills behind the camera as directors, making movies like Hot Rod, MacGruber and the upcoming The Watch. But does Samberg have a future behind the lens as well?

I recently had the chance to sit down one-on-one with Samberg, who stars in this weekend’s new release, That’s My Boy, and spoke with him not just about a potential career in directing, but also the challenge of playing the straight man, being a comedian versus being an actor, and taking on more dramatic roles. Check out the interview below!

Had you met Adam Sandler before this movie? And what was it like working with him?

I had met him a couple times. When I first got hired on SNL he called me out of the blue and was like [doing Adam Sandler impression], “I just wanted to say you’re doing a great job and I just figured were so similar I should say hi,” which for me, at that time, was like three or four shows in. And he was like one of my teenage heroes so I was freaking out. “Tell Hader you and him are doing a great job.” I told Bill and he was like, “Oh my god!”

And then I’d met him a couple other times. Me and my Lonely Island buddies, Akiva and Jorma, we went in for a general meeting at Happy Madison, hung out with him and some of his buddies there and just talked to him about the biz. [Doing Sandler impression again] “Well, if you ever have a movie idea!” And then I’d see him here and there, at like award shows and he’d come to SNL every now and again. And then I heard about this script and I called him a couple times to be like, “Hey…let me do this! [laughs] Are you doing that movie because I feel like I’d be really good for that movie.” And he was very sweet about it, he said he didn’t know if he was doing it and then it came together.

And once we started shooting it was like… I’ve been describing it as fantasy camp. If you want to go be an astronaut you go to Space Camp. For me I was in the zero gravity room all summer watching Sandler work and getting to subtly coerce him into doing old bits from SNL.

Did anything take you by surprise working with him?

His work ethic is through the roof, I will say that. People like him and people like [Ben] Stiller, you always hear their friends when they get interviewed, “They’re successful because they work harder than everyone else. That’s just it.” And you’re like, “Yeah, I’m sure, I’m sure, I’m sure.” And then you work with them…oh no, they actually work hard [laughs]. I’d be like, “Alright man, that was a rough day I’m going to go home.” And he was like, “Alright cool, I’m going to work on a script for another movie. It was like “What?! It’s like four in the morning!” “I know, I know.” But he kills himself for it. He loves it and he works hard every day on set. He’s constantly like, “How do we make this better?” He’s always really involved with the director and making sure that all the shots are tracking and the comedy is playing, and having done so much pre-taped stuff myself with the shorts and basically working as a self-contained film unit with Akiva and Jorma, I definitely related to that and it was nice to see that working on a much bigger scale. They still keep it tight. It’s still their creative unit and he’s making sure he makes it the way he envisions it. It was definitely educational for me.

To talk a bit about playing Todd in this movie, is it a fun change of pace to get to play the straight man?

For sure. I was worried about it going in because I was like, “I don’t know if anyone sees me as anything but a screaming or rabid person [laughs]. But it was made much easier because I was playing against him playing such a nutjob. This character is such a throwback to his old stuff. I’ve been saying to people who used to love his albums that it’s kind of like “Tollbooth Willy” meets some other guy from his record. He’s like a happier Tollbooth Willy. So when somebody’s coming with that much loose crazy energy playing uptight against that is actually fun. You can get laughs off of just making the right reaction face. And the director, Sean [Anders], was really sweet to me. “I want to make sure we get you not being into this so that the audience knows that it’s okay to also find him a little bit crazy or despicable in this moment. And that’s basic comedy straight man/crazy man, or whatever. Going in I thought it was going to be a bigger challenge than it was. I think that the trickiest stuff performance-wise for me was playing the “covering up a lie” kind of scenes. That stuff has always been…I’ve never had to actually do that. I’ve always kind of looked down on my nose on that stuff, but then when you’re in a scene trying to really make it work it’s like, “Oh, there really is an art to this,” where it’s almost like that sitcom freneticism of like, [in nerdy voice] “Uhm uhm uhm, the reason was that…” making up a lie on the spot kind of scenes. But I’m proud of the movie. When I watched it back I laughed a lot. I was like, “This is pretty good!” And I like that my guy starts off super uptight and you kind of get to see him loosen up a little. It’s much more fun.

That kind of leads me to my next question. There is a lot of stuff that happens to you in this movie that is just textbook horrible. When you’re preparing for scenes like that do you just have to shut off a part of your brain and just go for it?

A little bit, yeah. There’s definitely some stuff that’s raunchy in the movie and I definitely do dirty, like in the shorts we’ve done a lot of dirty and I love barf jokes and stuff, but there’s also some stuff wherein I was shooting this movie and was like, “Oh, this is straight up raunchy” [laughs]. And I think they found a good balance for it in terms of it feels organic to the movie, but while shooting there definitely are moments where they call cut and you’re covered in sticky tissues. “I hope people laugh at this shit!” But the amount of things I’ve done for comedy already is like…there’s not much left that makes me super uncomfortable.

Do you have a line?

I don’t know. I guess I haven’t been boned by a dude on camera [laughs] That’s funny right?! That’s something to look forward to! Yeah, that would probably have to be something that I would really have to psych myself up for. [laughs]

To bring it back to Todd, did the character change much from the script you first got to what we see in the final cut?

Not huge. More just like… I think I got to call things out a little more. There’s something I like about how my guy comes across. By the end he’s kind of saying things for the audience. At some point there’s some line about, some racist line where you’re supposed to find a person despicable for saying it, Todd gets to be like, “Well, that’s inappropriate.” Stuff like that. “I’m glad someone in this scene is saying it’s not cool to say that.” Just so we’re borderline socially responsible [laughs]. It’s good to have a balanced vibe of characters in a room, especially when it gets so crazy like it does in this movie.

To talk a bit about your career, Sandler is one of those comedians who has been known to occasionally do something a bit more serious, like Punch Drunk Love or Reign Over Me or even Funny People. And I know you also have Celeste and Jesse Forever coming out this summer, which is a bit more dramatic, but is that something you could see yourself continuing to pursue?

Absolutely. I had a blast shooting that other movie wish Rashida [Jones] and Lee Krieger. It was awesome. And certainly, Punch Drunk Love is one of my favorite movies. It’s like the perfect love story and Sandler is so good in it. If I was ever able to be a part of something that good, it would be killer. To get to work with someone like Paul [Thomas Anderson] too. He’s just like straight up genius. That trailer [for The Master]looks good!

That thing blew my mind.

I was like, “This looks like it’s from the 70s.” It almost feels like The Shining or something. I don’t know what it’s about yet!

Just that still shot of Joaquin Phoenix…

God, he looks for real crazy! The tone of it and you can tell that the scoring is going to be all good again. I just love his movies. I’m excited to see that.

Do you see yourself as a comedian or an actor, or is it something that kind of meshes in your mind?

Comedian. I’ve definitely always seen myself as a comedian mainly because I write. I’ve always taken as much if not more pride that I write than that I act. I have a lot of respect for actors, they’re really good, but I also feel like comedians have generally taken a different path to acting. And I really enjoy acting. It’s a new kind of weird challenge for me, doing Celeste and Jesse, even doing this movie and finding new ways to try and be funny and work out a character. But if I had to choose definitely comedian over actor [laughs].

To take that one step further, both Akiva and Jorma have started directing features as well. Is that something that you’d be interested in as well?

I don’t think that I would want to.


It’s so much work [laughs]. It’s so much multitasking and I feel I’m better sort of helping with writing and being on camera. I’ve worked with really great directors. Akiva and Jorma alone, it’s incredible how great they are. And Sean Anders on this was really good, Lee was great, John Hamberg on I Love You, Man, I think he’s a really great director. And other guys who have directed shorts and the show too. Jonathan Krisel did a bunch and now he’s doing Nick Kroll Show and Portlandia. This guy Jake Szymanski and John Solomon. When I look at them and I work with them I can see that it comes easy to them. Whereas for me I feel like thinking about the angles of the shots and all that stuff gives me a headache [laughs]. “Let’s just make the joke.” I’m always much more focused on, “Is it funny? Is it funny?” And the people who are actually good at directing, I’d rather let them do it. It’s like on a basketball team or something. “I could shoot a three-pointers, but we have that guy who is really good at shooting three-pointers, so I’m just going to hang out in the paint and lay it up.” [laughs]

NJ native who calls LA home; lives in a Dreamatorium. A decade-plus CinemaBlend veteran; endlessly enthusiastic about the career he’s dreamt of since seventh grade.