Video/Q&A: 'That's My Boy' star Andy Samberg

I guess I started thinking about it just this past season. The contract when you first get signed for the show is seven seasons, and I knew that I was going into my seventh season. I didn’t really know until I was on the phone with Lorne saying it because no matter when you leave it’s going to be the hardest decision you make.

Did he try to convince you to stay?
Not really. He’s been through it so many times, I think it was definitely more emotional for me than it was for him. I think if I had wanted to stay he would have been cool with that too. The show always finds a way. He’s got an eye for talent and I’m excited to keep watching it, and I love everybody there. I’m going to miss everybody a ton. I’m eternally grateful to have been on it. When I first got hired I would tell people it’s like when you’re a kid and you’re like, “I’m going to be an astronaut or I’m going to be shortstop for the Yankees." Things that just don’t happen actually did happen for me. It was insanely awesome.

What, if anything, would have had to have happened to make you want to stay?
I don’t know. I don’t know exactly even how to answer that. It just sort of was a decision I made. It wrapped up nicely for me with the 100th short and “Lazy Sunday 2.” I’m excited to maintain a relationship with the show. And we’ll see what happens.

You said this might not be the end of digital shorts for you. Care to elaborate?
Well, we’ll see. It’s obviously totally open-ended right now. I’m not going to be in the cast, but my hope is that there’s times for me to come back if Lorne would have me. That’s going to depend on what’s going on with the show at any given moment, and week to week. I also hope that we make another Lonely Island record. If we make videos for that, I would love to have them still air at "SNL". I always consider that my first home. I don’t want to put any pressure on Lorne. Whatever he wants to do. We’re going to keep making short-form videos that are both musical and comedic in some way, shape or form.

And if they want to air them great, if not that’s OK too.
Yeah. There’s always YouTube. And possibly both.

You grew up loving Adam Sandler films. What about his movies do you like, and have you continued throughout his career? You mentioned this movie hearkening back to his early movies. Have you liked the new stuff as much as the old stuff?
I have. Certainly my sensibility, if you know any of my work, is a little closer to his earlier stuff. A little more wacky, surreal, dirty, etc. But I’ve enjoyed his other movies a lot. One of the crazier movies he’s made recently is “[You Don't Mess with the] Zohan,” which I love. That movie made me laugh a lot.

That made me laugh a lot too.
He high-fives a pelican within five minutes. It’s like, “Oh, yeah, this is my kind of movie.” [Laughs] But this movie definitely is the craziest thing he’s done in a while. It’s exciting because he wears many hats. He can make family movies, he can make dirty movies, he can make “Punch-Drunk Love,” which is in my opinion one of the best film films made over the last 10 or 15 years. It’s an incredible movie and he’s incredible in it. He has that range and he chooses to try a bunch of different things. I appreciate what he does in all of them in a different way. But from a comedy perspective this is my favorite version. [Laughs]

Do you think people take stuff like this too seriously? I’m sure people are already grumbling about the teacher-student relationship in "That's My Boy," and this wouldn’t be the first Adam Sandler movie you could look at where overweight characters generate some laughs or there are some potentially sexist views, depending on who’s watching. Should people forget it and laugh?
I think if that’s the kind of thing that bugs you, this probably isn’t your taste. Everyone has their own personal sensibility. The Happy Madison movies are a very specific tone. This one certainly is the closest in a while that is mine, I would say, which is why I was so excited to do it. Like it was definitely the version of Sandler that I connect with the most. I enjoy all of his stuff in different ways. To be upset about a movie like this would be to be upset about a movie like "Wedding Crashers" or "The Hangover" or something. It’s a hard-R, shocking, crazy party movie, that’s just what it is. If you’re in the mood for that, crack a brewski and go to the theater. And I feel like the majority of people that see it do really enjoy it and laugh their asses off. My family came to the premiere. They’re not uptight, but my mom’s in her 60s and she laughed her ass off.

Your dad didn’t say, “I should have been in this”?
[Laughs] Comes full circle. He got ripped off. He should have played Donny Burger.
Where he ate last night in Chicago: "I went to Lula Café last night. It was delicious. [We ordered] all kinds of schnizz. I had the duck, it was delicious. We had some kale. Had a couple cocktails. I’m not going to front. I’m not going to front on you. My dream is to go to Schwa. I’ve been waiting to go to Schwa and it’s been hard. Because I’m barely here for a lot of time ever but that’s my main goal in life at this point."
The chances Justin Timberlake will ever be an "SNL" cast member, even for a year: "Zero. [Laughs] He doesn’t need to. He can just show up and destroy it and have everyone talk about him for 10 years ... There’s a lot of people that are super talented that have other careers already. [Laughs] I think Timberlake's probably making pretty good money doing other stuff."
Guilty pleasure movie: “Gosh. If you say it’s guilty pleasure it’s implying it’s not good. I mean I always like to talk about ‘Spaceballs.’ And ‘UHF.’ Those are two movies that I feel like are under-appreciated for how funny they are. What was the one with James Van Der Beeek with football? ["Varsity Blues."] I like that one. Me and Akiva used to watch that one. It’s just entertaining. High school movies are entertaining. You can’t help it.”
A question he's always wanted to ask Conan: "[Laughs] I don’t know. Conan’s done so many incredible things, man. I’d love to just talk to him for hours about working at “The Simpsons” or early “SNL” when he was there. He’s been a part of so many legendary moments in comedy at different places, including his own show, so there’s pretty much no shortage of things I could ask Conan. [Laughs]"

Watch Matt on “You & Me This Morning,” Friday at 7:30 a.m. on WCIU, the U @mattpais