This is no put-on. Samberg loves the movie about which Roger Ebert wrote, “I did laugh, but not enough to recommend it” — as damning a put-down as possible. Wrong, says Samberg: “There are some really funny jokes in there.” And who are we to argue with the man who made “Lazy Sunday” an Internet sensation and got Michael Bolton to dress as Captain Jack Sparrow and got 59 million pairs of eyeballs to watch him do “The Creep” with Nicki Minaj and John Waters on YouTube?
But those days of live TV and digital shorts may be coming to an end. At the time of this writing, Samberg was finishing his seventh and final contracted season on Saturday Night Live. Things have changed: Schaffer and Taccone, who were hired with Samberg as writers, are now off working on their own projects. And while Samberg still makes the occasional digital short, he’s more often than not found on the live show, playing an ensemble character or doing a slightly crazed Nicolas Cage during “Weekend Update” (once with Nicolas Cage, and it was brilliant). Having reached a crossroads of where he’s been and what’s to come, he’s pondering his inevitable future, which at the moment looks bright, whichever way he decides to go.
In addition to That’s My Boy, Samberg also appears alongside Rashida Jones in Celeste and Jesse Forever, a Sundance favorite in which the I Love You, Man cast members prove you can never be just friends with someone you once truly, deeply loved. It’s comedic, but not silly — the first step toward not being the guy who makes pants jokes with Justin Timberlake on the other side of the midnight hour.
“It is scary,” he says when asked what happens when it’s time to leave the show, which could happen sooner rather than later. “You don’t know if it’s going to work or not. I talk about when the time comes that I do leave SNL, there’s no guarantee it is going to work outside of there. You just don’t know.” He’s solemn now, but not serious. Giving up your dream is hard, especially when it has also become your home.
“If I give it my best shot, I might be in a position to make my movies,” he says. “And there are people who have that opportunity and for whatever reason it doesn’t come together for reasons beyond [their] control. You just never know.”