In a special standalone episode, David Letterman engages in a captivating conversation with Adam Sandler, exploring the comedian’s evolution from stand-up artist to Saturday Night Live (SNL) sensation and ultimately, a movie star. This special episode sees Letterman and Sandler having a heartfelt discussion both in front of an audience at New York University (NYU) and backstage before a performance at Mohegan Sun. Their mutual admiration is evident, raising the question: does this affection enhance or hinder the interview? Perhaps a bit of both.

Opening Scene: The camera pans across the vast, empty arena of the Mohegan Sun casino and resort in Connecticut, setting the stage where Sandler was slated to perform earlier this year.

The Essence: The interview is a dynamic blend of settings, featuring conversations at Mohegan Sun and in front of students at Sandler’s alma mater, NYU. The narrative fluidly shifts between these venues, offering a rich tapestry of insights into Sandler’s career and personal journey.

A consistent theme throughout is the mutual respect and admiration between Letterman and Sandler. Letterman is generous with his praise, and Sandler reciprocates by acknowledging Letterman’s influence, declaring him a hero to his generation of comedians.

The conversation unfolds in a chronological manner, beginning with anecdotes from Sandler’s early years. He recalls his father gifting him a Fender Stratocaster at the age of 12, a guitar he still plays during performances. From there, the discussion transitions to Sandler’s teenage adventures as he ventured from his hometown of Manchester, New Hampshire to Boston, marking the start of his journey into stand-up comedy.

We learn Sandler was a “Wedding Singer” even as a teen at his sister’s wedding (dad approved); that he didn’t know acting could be a major in college; that he didn’t plan for his first stand-up gig (“I do remember I was devastatingly bad and nobody laughed”); yet he was cocky and determined enough to place high expectations upon himself, boasting to friends in New Hampshire that he’d one day be as big as Eddie Murphy. We also learn that fate or fortune made him NYU roommates with Tim Herlihy (who’d go on to co-write many of Sandler’s movies, and whose son Martin made it to SNL, too), with Sandler saying Herlihy began writing jokes for him after their very first weekend at NYU.

At Mohegan Sun, Sandler talked about his pre-show routine, which includes finding a court for pickup 3-on-3 hoops. He also recalled both his last show with the late Norm Macdonald in 2016 (at the Connecticut casino/resort), as well as Sandler’s first performance on Letterman’s Late Night back in 1991. We see a short clip from that set, but here’s the full version of Sandler’s network TV debut!

Sandler hits the early highlight hallmarks, including filming an episode of The Cosby Show as Theo’s friend Smitty while Sandler was still enrolled at NYU, rooming with Judd Apatow when he moved to Los Angeles after college, and the joke that Sandler told that got Lorne Michaels to laugh during his SNL audition.

There’s a chunk where Letterman focuses on Sandler’s dramatic turns in Punch-Drunk Love and Uncut Gems, with Letterman suggesting the Academy Awards should include an annual segment to acknowledge their past mistakes in snubbing great performances like Sandler’s.

They also joke about how Letterman only made fun of the comedians he loved on his late-night shows, and how they both fared during the Mark Twain Prize ceremony for Conan O’Brien earlier this year.

What Shows Will It Remind You Of?  This episode is a blend of Inside The Actor’s Studio with a 60 Minutes puff profile, only with Letterman’s trademark wit underpinning it all.

Our Take: Each of Letterman’s first five seasons of his Netflix series have earned him an Emmy nomination, and took home the Emmy for Outstanding Hosted Nonfiction Series or Special in 2024.

This standalone episode, however, stands out for less than award-worthy reasons. The structure of the episode isn’t linear, and the conversations sometimes overlap with Sandler repeating stories in slightly different ways. Perhaps the opening scene could’ve warned us that this episode might not be going as hard as we want, with Letterman quipping after Sandler’s first story (Where he learned how to play “Malagueña” note-for-note to earn his Fender): “We don’t need anything more from you than that story about your dad buying you that guitar, and you working with it every night. So you and your dad are still onstage. That’s fantastic…So we’re done here. That’s a wrap.” 

More awkward, though: Letterman veering off course multiple times in their conversation to spotlight work Sandler has done for Netflix this year, from Happy Gilmore 2 to the upcoming Jay Kelly, and the Mark Twain Prize special.

What was it like working with George Clooney on Jay Kelly? Who cares?!? I thought we were here to learn more about Sandler?

But Netflix must be happy about all of this in-house promo. So there’s that, I guess.

Our Call: I’d say STREAM IT just for the tidbits we learn from Sandler’s earliest forays into comedy, although it’s also supremely frustrating to see this episode turn from entertaining or incisive interview to straight advertorial for Netflix’s programming.

Sean L. McCarthy works the comedy beat. He also podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.