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Samberg (center) with Vanilla Ice (left) and Adam Sandler in That’s My Boy.
Tony Rivetti/Sony Pictures

Several times throughout our interview, Samberg describes working with Sandler as “a dream come true.” There are, he explains, several reasons for this, chief among them: 1995’s Billy Madison, the first of Sandler’s many films about the Stunted American Male.

“When I was in late high school, early college, I was so obsessed with Billy Madison that I would listen to it on audiotape on my Walkman,” Samberg says, his deep-felt sincerity and affection­ audible over the roar of the upstairs crowd. “Billy Madison was my bible.”

He mentions other films that were personal touchstones: Sandler’s Happy Gilmore, the first Ace Ventura: Pet Detective, and Tommy Boy, an SNL-veteran twofer starring David Spade and the late Chris Farley. ­Samberg says those movies just hit him at the right time: the mid-’90s, when he was about to graduate from Berkeley High School in Berkeley, Calif., and make his way to film school at New York University and, eventually, to the stand-up clubs, writing gigs, Internet memes and television fame. Maybe those movies aren’t considered comedy classics the way Duck Soup is, or It Happened One Night or Annie Hall or Tootsie. Didn’t matter. All Samberg saw was young men acting stupid and making money. And that he liked.
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Those films, he says, are “so specifically what I find funny,” and they “made me think for the first time — like, for real — that I could do it. Because if these guys can make it, and if what they do, which I find so funny, is also considered funny by other people, I think I have a shot at actually working in comedy. I’ve told that to Sandler, and I’ve told it to Jim Carrey.”

The first time Samberg actually spoke with Sandler was sometime in the fall of 2005.

Samberg was 13 when a then-25-year-old Sandler made his SNL debut. Just as Sandler became known for characters ranging from Canteen Boy to Opera Man to the ­Herlihy Boy (each a various shade of dim), years later, ­Samberg would follow in his idol’s footsteps by creating that most special of stocking stuffers with Justin Timberlake during one very famous Christmas episode in 2006 — a bit that won him an Emmy.

“Sandler called me at SNL my third or fourth week there,” says Samberg, who joined the cast with Bill Hader, an Oklahoman whose ability to mimic ­bygone acting greats is, occasionally, startlingly creepy. Samberg and Hader appeared together on their first episode: Oct. 1, 2005, introduced to the world by Amy Poehler during a “Weekend Update” segment called “Friendly New Guy Impression-Off.”