My Next Guest with David Letterman and Adam Sandler: A Homecoming King Returns to Court

In a year that has seen Adam Sandler break streaming records with a return to his comedy roots and court Oscar buzz for a nuanced dramatic turn, his latest project feels less like a press stop and more like a victory lap. My Next Guest with David Letterman and Adam Sandler, premiering December 1 on Netflix, reunites the comedy icon with the legendary late-night host for a standalone special that is as much about the craft of comedy as it is about the man behind the voices.

Filmed at New York University—Sandler’s alma mater and the city where he cut his teeth in stand-up clubs before his Saturday Night Live breakout—the special offers a setting that is both intimate and grand. It’s a fitting backdrop for a conversation that spans decades, from the chaotic energy of the early 90s to the reflective stature of a Hollywood mogul who has nothing left to prove.

The Letterman Connection

David Letterman’s post-retirement chapter with Netflix, My Next Guest Needs No Introduction, has always thrived on a specific kind of chemistry. Freed from the constraints of network commercial breaks and the nightly grind, Letterman has evolved into a more patient, albeit still sharp-witted, interviewer. His rapport with Sandler is evident from the moment they sit down.

This isn’t their first rodeo. Sandler was a frequent guest on The Late Show, where his appearances were often marked by a chaotic charm—wearing oversized t-shirts, playing guitar, and generally treating the Ed Sullivan Theater like his living room. In this special, the dynamic has shifted. There is a mutual reverence. Letterman, the elder statesman of comedy, seems genuinely curious about Sandler’s unique trajectory: a comedian who was critically reviled for years while being beloved by audiences, only to eventually win over the critics without changing his essential nature.

A Year of Dualities: Happy Gilmore 2 and Jay Kelly

The timing of the special is no accident. 2025 has been a banner year for Sandler, showcasing the two distinct poles of his career. Earlier this summer, Happy Gilmore 2 arrived on Netflix, shattering opening-weekend records. The sequel to the 1996 classic saw Sandler slipping back into the hockey jersey of the rage-fueled golfer, proving that his brand of slapstick and man-child rage still resonates with a massive global audience.

But just as the laughter from Happy Gilmore 2 was settling, Sandler pivoted. In Noah Baumbach’s Jay Kelly, released in select theaters in November and hitting Netflix globally on December 5, Sandler plays Ron Sukenick, the devoted manager to George Clooney’s titular character. The role has garnered Sandler some of the strongest reviews of his career, with critics praising a performance that is quiet, desperate, and deeply human.

Letterman presses Sandler on this duality. How does one go from fighting Bob Barker (or his spectral equivalent) to holding his own against Clooney in a Baumbach script? Sandler’s answer, typical of the man, is self-effacing. He speaks about “trusting the friends” he works with, whether it’s Tim Herlihy on a comedy script or Baumbach on a drama. Yet, the special reveals a deliberate artist who knows exactly which lever to pull and when.

The NYU Factor and the Guitar

One of the special’s most poignant segments involves Sandler discussing his time at NYU. Walking the streets of Greenwich Village with Letterman, Sandler reflects on the hustle of his early twenties—the open mics, the bombed sets, and the relentless drive to be funny. It’s a grounding element that reminds viewers that before he was a billion-dollar box office guarantee, he was just another kid from New Hampshire trying to make New York laugh.

And, of course, there is the guitar. No Sandler appearance is complete without music. The special features Sandler with his Stratocaster, but rather than the silly, gibberish songs of his youth, he offers something more melodic and reflective. It’s a callback to his acclaimed 2018 special 100% Fresh, where his musical tribute to Chris Farley became a viral tear-jerker. Here, the music serves as a bridge between the jokes, a way for Sandler to express emotions that he might otherwise deflect with a punchline.

Production and Direction

Directed by Michael Steed, who has helmed much of the My Next Guest series, the special maintains the show’s high visual standard. The editing allows the conversation to breathe, lingering on reactions and silences that a network show would cut. Produced by Jax Media and Letterman’s own Worldwide Pants, the special feels polished but authentic.

Executive producers Tom Keaney, Mary Barclay, Justin Wilkes, and Yolanda T. Cochran have crafted an episode that fits seamlessly into the prestigious lineage of the series, which has hosted figures ranging from Barack Obama to Volodymyr Zelenskyy. By placing Sandler in this pantheon, the show implicitly argues that he is not just a movie star, but a significant cultural figure.

Release Date

My Next Guest with David Letterman and Adam Sandler is a must-watch not just for fans of the actor, but for anyone interested in the mechanics of fame and comedy. It captures a moment in time where Adam Sandler is arguably at the peak of his powers—comfortable in his legacy, daring in his new work, and still able to crack up David Letterman with a well-timed look.

As Season 6 of My Next Guest looms on the horizon, this standalone special serves as a perfect appetizer. It reminds us why Letterman is the master of the form, and why Sandler, after all these years, is still the guy we want to hang out with.

Where to Watch: My Next Guest with David Letterman and Adam Sandler streams on Netflix starting December 1, 2025.

Netflix