Dave’s face changed. It didn’t just age; it transformed. If you scroll through old pics of David Letterman from the early eighties, you see a guy who looked like a nervous insurance salesman with a gap-toothed grin. Fast forward to 2026, and he’s basically a biblical prophet who happens to enjoy IndyCar racing.
People are obsessed with these photos because they document a rare thing: a celebrity who actually stopped caring about the "celebrity look."
Most of us grew up with the clean-shaven Dave. The guy in the double-breasted suit. The guy who wrestled with a giant tub of popcorn or wore a suit made of Alka-Seltzer. But honestly, the retirement photos—the ones where he's jogging in St. Barts with a beard that would make a Civil War general jealous—those are the ones that went viral for a reason. They represent a total break from the "Late Night" grind.
The Evolution of the Letterman Look
It’s kinda wild to look back at the NBC years. In those early pics of David Letterman, he had this thick, dark hair and those signature glasses that screamed 1982. He looked sharp, but also sort of frantic.
Then came the CBS era.
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The suits got more expensive. The hair started to thin a bit, turning that distinguished salt-and-pepper. You’ve probably seen the iconic shot of him and Paul Shaffer on the final night in 2015—Dave looks exhausted but happy. It’s a classic piece of TV history. But the moment he walked out of the Ed Sullivan Theater for the last time, the razor went into the trash.
The "Retirement Beard" Era
When the first paparazzi shots of the beard hit the internet, people genuinely didn't recognize him. He looked like an "aging vagrant," which is actually how he described himself on Jimmy Kimmel Live! a few years back.
- The Santa Phase: Around 2016, photos showed him with a bushy, white beard and a bald head. The internet immediately compared him to Santa Claus or a guy who had been living on a deserted island for a decade.
- The Marathon Man: There are these great shots of him running. He’s usually wearing yellow shorts and looks like he’s having the time of his life.
- The Statesman: By the time My Next Guest Needs No Introduction premiered on Netflix, the beard had become "The Beard." It was groomed. It was majestic. It signaled that this wasn't the guy who was going to do Top Ten lists anymore.
Iconic Moments Captured on Camera
There are certain pics of David Letterman that every fan knows. Like the one from 1995 where Drew Barrymore jumped on his desk and flashed him for his birthday. Dave’s face in that moment—stunned, slightly terrified, yet professionally amused—is a masterpiece of candid photography.
Or the photos with Bill Murray. Whenever Bill showed up, things got weird. There’s a famous shot of them playing football in the middle of 53rd Street. It captures the chaotic energy that defined Dave’s prime. You can feel the New York humidity and the smell of exhaust just by looking at it.
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Then you have the Annie Leibovitz portraits. Those are different. They aren't candid; they’re art. They capture the cynical, intellectual side of Letterman that he usually hid behind a joke about a "Stupid Pet Trick."
Why We Still Search for These Images
Basically, we're looking for signs of life. Late-night TV feels very "produced" now. Everything is a viral clip designed for TikTok. But Dave? Dave was dangerous. Even in a still photo from a 1984 episode with Cher, you can see the tension.
He didn't always want to be there, and that made the photos interesting.
The most recent pics of David Letterman from late 2025 and early 2026 show him popping up at comedy clubs or sitting courtside. He looks comfortable. He’s not wearing the suit. He’s wearing hoodies and sneakers. It’s a weirdly inspiring visual narrative of a guy who did his time, won the game, and then decided to just be a person.
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How to Find the Best High-Res Letterman Photos
If you’re looking for high-quality archives, Getty Images is the gold standard, though it'll cost you. For fans just wanting a nostalgia hit, the official Letterman YouTube channel and Instagram often post "throwback" stills that haven't been seen in decades.
- Look for the NBC era (1982-1993): These have the best "indie" energy.
- Search for the "Strike Beard" of 2008: A rare preview of his current look during the writer's strike.
- Check Netflix press kits: For the most recent, high-definition "Wise Elder" Dave shots.
Honestly, the best way to appreciate these photos is to look at them chronologically. You see a man go from trying to prove himself to the world to not caring if the world even knows who he is.
If you want to dive deeper into the history of these moments, your best bet is to check out the "Late Show" archives or the Ball State University digital collection, which houses a ton of his personal memorabilia and photography. It’s a fascinating look at the most influential guy in the history of the medium.
Actionable Insight: Next time you see a "retirement" photo of Dave, look at the eyes, not the beard. You'll notice he looks way more relaxed than he ever did behind that oak desk in Manhattan.