Let’s be honest: modern late-night TV feels like a series of viral TikTok clips stitched together with forced laughter. It’s polished. It’s safe. It’s fine, I guess? But if you grew up watching the Late Show with David Letterman, or even just caught the tail end of it on CBS, you know something massive is missing from the current landscape.
Dave was a weirdo. He was prickly, occasionally rude, and deeply uncomfortable with the very idea of being a "showbiz" guy. That’s exactly why we loved him.
The story of the Late Show with David Letterman isn't just about a guy in a suit behind a desk. It’s about a messy, high-stakes corporate war that changed television history and a man who spent 33 years trying to deconstruct the medium he was the king of.
The Night Everything Changed: The NBC Betrayal
Most people know Dave moved from NBC to CBS in 1993, but the "why" is where the real juice is. For years, Letterman was the heir apparent to the legendary Johnny Carson. He hosted Late Night at 12:30 AM, directly following Carson’s Tonight Show. He was the protégé. The cool, edgy younger brother.
When Carson announced his retirement, the world assumed Dave was getting the keys to the kingdom.
Instead, NBC gave the job to Jay Leno.
It was a cold-blooded corporate move. Leno’s management was aggressive, and NBC executives thought Dave was too "difficult" or "ironic" for a mainstream 11:30 PM audience. They wanted vanilla; Dave was a jalapeño-infused bourbon.
So, Letterman walked.
He didn’t just leave; he took his talents to CBS, who bought the Ed Sullivan Theater for him and basically gave him a blank check. On August 30, 1993, the Late Show with David Letterman premiered. The vibes were electric. Bill Murray was the first guest, and he was as chaotic as you’d expect.
What Made the Show... Weird?
The "Late Show" was technically a talk show, but it often felt like a parody of one. While Leno was doing "Jaywalking" and telling safe jokes, Dave was busy dropping watermelons off five-story buildings.
He didn’t care about being liked.
Remember the Top Ten List? It’s a staple now, but back then, it was a brilliant way to mock the very idea of topical humor. He had segments that made zero sense on paper. "Stupid Pet Tricks" was exactly what it sounded like—dogs doing weird stuff. "Is This Anything?" featured people doing bizarre acts while Dave and Paul Shaffer watched with a mix of awe and contempt.
And we have to talk about Paul. Paul Shaffer wasn’t just a bandleader; he was the perfect foil. His glitzy, "showbiz" energy contrasted perfectly with Dave’s Midwestern cynicism. The CBS Orchestra was arguably the best band in the history of television. Period.
The Guests He Actually Liked (and the ones he didn't)
Dave was a legendarily tough interviewer. If he thought a celebrity was vapid or phoning it in, he’d let them hang themselves with their own words.
- Joaquin Phoenix: The 2009 appearance where Phoenix was "quitting acting" to become a rapper. Dave’s reaction? "Joaquin, I'm sorry you couldn't be here tonight."
- Madonna: In 1994, she came on, used a certain four-letter word 14 times, and handed him her underwear. Dave just sat there, amused and slightly horrified.
- Tom Hanks: These two had actual chemistry. It felt like two friends catching up.
- Drew Barrymore: The 1995 birthday dance on the desk. You know the one. Dave’s face was a masterpiece of "I have no idea what to do with my hands."
The E-E-A-T Factor: Why the Industry Respects Him
If you ask any modern host—Conan O’Brien, Jimmy Kimmel, Seth Meyers—they’ll tell you Dave is the blueprint. Bill Carter’s book The Late Shift details the insanity of the Letterman/Leno rivalry, and it’s a masterclass in how TV works behind the scenes.
🔗 Read more: Why I Was Gonna Clean My Room Became the Internet's Favorite Anthem for Procrastination
Letterman’s legacy isn’t just about the jokes. It’s about his honesty.
When 9/11 happened, Dave was the first major entertainer back on the air. His monologue wasn't funny. It shouldn't have been. It was raw, shaking, and incredibly human. He did the same thing when he returned from heart surgery, and again when he had to address his own personal scandals on air. He didn't hide behind a PR rep; he sat behind his desk and talked to the camera.
Why the Ratings Never Quite Matched the Legend
Here’s the truth: for most of their 22-year rivalry, Jay Leno beat Letterman in the ratings.
Why? Because Leno was easy. You could turn on the Tonight Show and have it on in the background while you folded laundry. Letterman demanded your attention. He was sardonic. Sometimes he was grumpy. He played to the "smart" crowd, the college kids, and the people who wanted their comedy with a side of bile.
But as Jay Leno famously said, "I got the numbers, and he got the critical acclaim."
The End of an Era
When David Letterman retired on May 20, 2015, it felt like the end of a specific kind of New York. The Ed Sullivan Theater felt like a cathedral. His final show featured five living Presidents and a "Top Ten" list delivered by his favorite regulars (Steve Martin, Tina Fey, Jerry Seinfeld, etc.).
He’s still around, of course, doing My Next Guest Needs No Introduction on Netflix. He’s got the big beard now. He’s mellower. He’s basically the cool, eccentric grandfather of comedy.
How to Appreciate the Legacy Today
If you want to understand why everyone still talks about this show, don't just read about it.
- Watch the 1982 NBC debut: It’s available in pieces on YouTube. See how different it was from everything else at the time.
- Look up the 9/11 monologue: It’s a textbook example of how to lead with empathy during a crisis.
- Check out the "World's Most Dangerous Band" clips: Paul Shaffer’s arrangements were lightyears ahead of what other shows were doing.
The Late Show with David Letterman wasn't just a 60-minute block of time. It was a nightly reminder that it’s okay to be a little weird, a little honest, and a lot skeptical of the world around you. Late-night television has become a lot more polite since he left, but it’s definitely a lot less interesting.
To truly dive into the history, track down a copy of Jason Zinoman's Letterman: The Last Giant of Late Night. It breaks down how the show's "irony" actually masked a deep, formalist love for the medium of television. Reading that book while watching old clips of Dave tossing a bowling ball into a vat of pudding is probably the best way to spend a Saturday night.