My Next Guest with David Letterman and Adam Sandler

The Melancholy of the Stratocaster

At some point Adam Sandler stopped being America's favorite overgrown goofball and became one of our steadiest screens for sadness. I still can't tell you the exact moment it happened. It kind of crept in, and then suddenly there it was. In Michael Steed's *My Next Guest with David Letterman and Adam Sandler*, the 2025 standalone Netflix special, that shift sits right out in the open. Sandler doesn't carry himself like a mogul. He folds inward. The clothes are, naturally, too big. His knees keep bouncing. His shoulders slope as if all the success in the world never quite reached the nervous system. Sitting across from Letterman, he looks like a man mildly baffled that anyone is still interested in him. Rationally that makes no sense. Emotionally, I got it.



The timing of this conversation is part of what makes it interesting. Sandler is in one of those weirdly perfect career stretches where everything is firing at once: major critical praise for his dramatic work opposite George Clooney in Noah Baumbach's *Jay Kelly*, huge streaming numbers for *Happy Gilmore 2*. Prestige and broad, goofy nostalgia are running side by side. Steed doesn't try to sand that contradiction into some clean thesis. The direction is loose, the editing wanders, and yes, it occasionally repeats itself. Letterman meanders and Steed lets him. Whether that shapelessness feels indulgent or generous probably depends on how much patience you have for two veterans circling the same questions until something real finally slips out. I didn't mind it. The slackness feels lived-in.



The moment I can't shake happens backstage at one of Sandler's tour stops, far from the tidy control of the NYU stage where most of the interview unfolds. He picks up his Stratocaster and you can almost watch the tension drain out of his neck. His hands fall into place without thinking. He knocks out a few loose chords, not to perform for Letterman, not even to make a point, but simply to settle himself. It made me think about the way comedians hide inside objects. The guitar isn't just there for the songs; it's cover. A wooden screen between Sandler and the dead air of a room. When he starts talking about getting laughs as a kid by imitating his grandmother, his fingers keep moving over the frets. The old need for approval is still humming underneath everything.



Letterman understands that fragility better than he sometimes lets on. He doubles back, he fumbles a phrase here and there, but the affection is unmistakable, and it steadies the whole special. Amy Davidson, writing for HuffPost UK, called it "a heartwarming combination of laughs and interesting tidbits" and an "ideal pre-Christmas warmer". That's fair, but it undersells the ache of the thing. What stays with me isn't the *Saturday Night Live* nostalgia or the tour through the famous roles. It's the sight of two private men, older now, realizing they survived the grinder. Sandler looks grayer, more worn down, and oddly more open. I don't think he's ever been this interesting to watch.