Thirty Years Later, How Well Does David Letterman’s First ‘Late Show’ Hold Up?

Thirty Years Later, How Well Does David Letterman’s First ‘Late Show’ Hold Up?

For 30 years, a group of friends and I, all of us big David Letterman fans, have invoked one particular phrase to differentiate ourselves from those who are merely fond of the venerable talk-show host. Nobody else catches the reference, which is fine with us. It’s a code for the real diehards, the kind of utter absurdity that was Letterman’s speciality. We even have his inflection just right.

“Where the hell are the singing cats?”

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That question was asked on August 30, 1993, the night of the very first episode of Late Show With David Letterman. For a lot of us, that was a pretty magical night — the evening that the King of Late Night would be officially crowned after being denied his rightful title for so long. It felt like a rare instance when one of “our” guys ended up on top — when the underdog, the class clown, the ordinary joe won the big prize. You didn’t just love Letterman — you loved what he represented. And 30 years ago today, his ascension was cemented. At least we thought it was. A lot changed after that.

I haven’t gone back to watch Letterman’s first Late Show since 1993, but I remember the details of that night vividly. I had just moved to college the week before, my new floormates and I bonding over our shared love for the gap-toothed Indiana funnyman. Eight days after I arrived on campus was his first show, which felt oddly perfect. I was in a new phase of my life, and so was Letterman. We watched the show, cheering on our smart-ass pal who had said goodbye to those NBC weasels — Letterman’s favorite term for executives who dared cross him — and jumped ship to CBS, setting the stage for the infamous late-night wars of the 1990s. It was Letterman versus Leno, and what self-respecting person would root for shallow, smiley Jay? Letterman was cooler. He deserved to be the GOAT.

Even though it’s been 30 years since I watched that first CBS episode, I felt like I had a pretty good memory of the show’s contents. Bill Murray was the first guest, and he proceeded to spray-paint Letterman’s first name onto the front of the desk so that this larger new audience would know who Dave was. There was a Top 10 list, which was far from a certainty considering that NBC tangled with Letterman over which of his bits were the intellectual property of his old network

And, of course, there was a moment early on when, apropos of nothing, Paul Newman stood up in the audience, the rest of the crowd roaring with applause at his surprise appearance. When the ovation died down, Letterman thanked him for being there, which prompted the faux-puzzled Oscar-winner to ask a question: “Where the hell are the singing cats?” Sorry, Paul, Letterman responded, this wasn’t Cats — this was his new show. Embarrassed, Newman realized he was in the wrong theater, quickly making a run for the exit. 

Endlessly amused at the non-sequitur pointlessness of the bit, Letterman spent the rest of the show mocking/recalling Newman’s question. Where the hell are the singing cats? It encapsulated what was so great about Letterman: The joke wasn’t necessarily sharp, but its bizarreness nicely deflated the evening’s pompous spectacle, the host snidely ridiculing the joke’s (and, by his extension, his own) shrug-emoji futility. Letterman hated chummy showbiz phoniness, and he brought out a big Hollywood star to drive the point home. Newman didn’t give a shit about Letterman’s much-anticipated debut on CBS — he wanted to see Cats.

If you look online, you can find that first Late Show on YouTube, so I decided to watch it for the first time in three decades, both curious and anxious. Like listening to live albums from shows you really loved or revisiting favorite childhood movies, there can be a jarring realization that comedy from the past just doesn’t hold up. Times change, pop-culture references lose their potency, what was funny might just seem super-cringe now. So I’m happy to report that Letterman’s maiden CBS voyage is no embarrassment. Sure, it’s not a pantheon episode, but it’s got its funny moments. At the same time, though, in retrospect you can see why Letterman’s late-night dominance wasn’t going to last. America was never going to fully embrace a show this surly and odd. But it was fun while it lasted.

For anyone who needs a refresher, before 1993, The Tonight Show was the preeminent late-night talk show, the one hosted by Johnny Carson, whose decades-long run ended when he announced his retirement in 1991. His last show was May of the following year, with his successor to be Jay Leno, whose peppy, polished guest-hosting gigs had endeared him to the NBC brass. Meanwhile, Letterman, whose Late Night aired right after The Tonight Show, was Carson’s preferred replacement. But Letterman was denied the gig that seemed to be his birthright, angering journalists, TV critics and comedy fans who considered Late Night a groundbreaking and brilliantly, weirdly hilarious talk show. Hoping to compete in late night, CBS made Dave an offer. Soon, the forthcoming battle was the country’s biggest media story. Would Jay or Dave emerge victorious?

We know that answer now, but we didn’t on August 30, 1993. All that was clear in those first few minutes was, good lord, it looked like Letterman and his team got a much bigger budget than they did on the old NBC show. One of the charms of Late Night, which aired at 12:30 a.m. Eastern time, an hour after The Tonight Show, was that it exuded the vibe of a hip cable-access show with better celebrity guests. Watching that show, it always seemed like Letterman was getting away with something — hurling himself onto a wall wearing a velcro suit, marveling as Chris Elliott ate dog food with a straight face, harassing GE executives — and the fun came from wondering if anybody would ever stop him. There was nothing upscale or “professional” about Late Night’s witty stupidity, which made it the polar opposite of the ingratiating, slightly sleepy Tonight Show. Letterman brought a snarl to late night, striking a chord with all the irony-drenched Gen-Xers in the viewing audience who saw in him an avatar for their own discontent with prepackaged Hollywood bullshit. 

It’s hard to remember now, but Letterman’s arrival on stage at the Ed Sullivan Theater that first Late Show felt like its own triumph. Sporting a spiffier suit than during the NBC years — and backed by a shiny, bigger new set — he wasn’t the upstart anymore. He was on at 11:30, maybe not on NBC, but this was a whole new show — a smart alternative to The Tonight Show, which long felt like it had a monopoly on the late-night format. Yes, there was The Arsenio Hall Show, too, but Late Show felt grander and more confident. Leno’s The Tonight Show was all neon L.A. glitz, while Late Show looked grownup and classy, hosted by a sarcastic wisecracker who loved to undercut the majesty of the famed theater where he now worked. (He joked on that first night that, when the construction team was refurbishing the place, they found some middle-aged lady accidentally buried in the walls who’d been there ever since the Beatles’ historic 1964 performance — which had taken place nearly 30 years before Letterman’s debut.)

Watching it now, everything about Letterman’s first CBS episode feels like a victory lap. The crowd immediately gives him a standing ovation, chanting, “Dave! Dave!,” which Letterman (in perfect Midwestern fashion) both seems to enjoy and is embarrassed about. (When the noise finally dies down, Letterman quips, “If you think about it, all I did was take the summer off.”) But the raucous response was understandable. This was like your favorite band going from club dates to playing arenas. Letterman is in this huge space! He’s big time now! 

But despite the fanciness, Letterman seems determined to lower expectations and crack jokes about the extravagance. A running gag was his annoyance at how many promos CBS aired advertising his new show. (“The Gulf War didn’t get this kind of coverage,” he quipped to Paul Shaffer.) When the producers ran a fancy new graphic in front of the Top 10 list, Dave deadpanned, “That’s about a million bucks right there.” (That the graphic now looks so incredibly cheap by modern TV standards only makes the joke funnier.) NBC’s nightly news anchor Tom Brokaw comes on during the monologue, not to congratulate Letterman but to take two of Dave’s cue cards that contain jokes, Brokaw says, that belong to NBC. “Who would have thought you would ever hear the words ‘intellectual property’ and ‘NBC’ in the same sentence?” Letterman sneers after Brokaw walks off. Also making fun of CBS — there’s a Murder, She Wrote joke in the monologue — Letterman wants to make it clear he hasn’t changed. He hasn’t go showbiz, even if his studio is now literally on Broadway.

If you checked out an episode of a random talk show from 30 years ago — hell, 10 or 5 years ago — it would probably be a series of peaks and valleys. It’s one of the great joys and limitations of late night, which is meant to be entertaining but disposable, ready to be discarded for the next evening’s jokes and guests. These shows are a grind to write and make, and especially back then, before the internet changed how we digest such programs, they were mostly something to watch before you went to bed — or, if you were like a lot of young people who worshiped Dave, you taped it on your VCR in order to watch during more reasonable hours. They’re not meant to be totems or time capsules. They’re a collection of hastily-written topical jokes and flirty banter that you barely remember afterward.

Letterman was 46 when he filmed that first Late Show, lacking the gravitas and faint whiffs of tenderness that would eventually surface later in his life once he embraced medication for depression and fatherhood for the restlessness he thought might be permanent. There’s little attempt to speak sincerely about the momentousness of the occasion — there’s only the silliness of bringing out the entire construction crew to thank them, or a classic Letterman remote segment in which he asks unreceptive New Jersey residents for ideas for the CBS show. (Predictably, and quite amusingly, most people think this Letterman guy is a doofus — if they even know who he is.) 

That said, it is a bit of a bummer that the first Late Show doesn’t have a lot of incredible moments. “Where the hell are the singing cats?” is still wonderful. But Murray’s appearance is mostly shtick, the Groundhog Day actor committing to bits that just aren’t that funny. (This, however, doesn’t apply to him taking forever to come on stage after his name is called, finally running on and out of breath: He went to the old studio, he explains betweens gasps.) As for Letterman’s first musical guest, I had completely forgotten who that was, then realized why I hadn’t remembered: Billy Joel came out to perform the supernally anonymous rock song “No Man’s Land” off River of Dreams, which was the No. 1 album at the time. (Fun fact: Joel hasn’t released a new studio record of pop/rock music since.) 

After the song, there’s a brief, awkward conversation between Joel and Letterman at the desk in which they seem to have absolutely nothing in common. At least Letterman could riff off Murray’s dying bits. When Murray tries to spray-paint the desk, the malfunctioning spray can adds to the evening’s principled half-assed approach — Murray can only get out a “D” and an “A” before basically giving up. Often, a joke on Letterman bombing was better than when it killed because it seemed to speak to the show’s underlying ethos, which was that this was all a waste of time. We didn’t mind that — we wouldn’t want to waste time with anyone other than Dave. With him, time-wasting was practically a political stance, an admission that so much of life was strained attempts to be self-important. Dave encouraged us to find the value (and the humor) in just farting around. Before Seinfeld, Letterman mastered the art of making a show about nothing. 

Did I remember that first night’s Loni Anderson joke? No, and I had to look up what it was in reference to. Was I thrilled to hear Letterman make cracks about Joey Buttafuoco? I was not, because it reminded me of the generally stupid, lewd jokes talk shows would make at the time about anything involving sex scandals. Even the program’s old-fashioned boxy aspect ratio — long before HD widescreen became the preferred format — speaks to what it hopelessly bygone about that initial Late Show

My 2023 mixed reaction to the episode was a huge disappointment to 1993 me — I could have sworn the CBS debut (and Late Show in general) was tremendous. And perhaps it was for the time. A lot of the epiode’s appeal was just getting to see Dave enjoy his moment in the spotlight. Taken for granted, not yet hailed as one of his era’s foundational comedy titans who inspired hundreds of comics and future talk-show hosts, Letterman seemed to be finally earning the props he’d been deprived of to that point. For a guy known for his pessimism and perfectionist streak, he actually seemed somewhat happy that night. 

Maybe the young me was loving not so much that specific episode but the idea of what Late Show was going to be — a confirmation that “we” were right about our Dave all along. The older me watched it knowing what was to come: the incredible post-heart surgery episode, the unforgettable monologue after 9/11, the night he told us about being extorted because he’d had affairs with female employees, the Warren Zevon episode, so many other highlights. But I also remembered how Late Show didn’t ultimately beat The Tonight Show, Leno’s ratings eventually overtaking Letterman’s. And as years went by, Letterman seemed increasingly less engaged by the show — he looked bored, frankly. He had moved on, but he was still sitting behind that desk. Dave achieved so much on late night, but you can’t do one of those programs without also delivering hour upon hour of episodes that just kinda stink. It’s inevitable, it’s baked into the format — you fail more than you succeed, although Letterman succeeded more often than others. But with that first Late Show, he still seems perfect.

At the same time, though, I see the Letterman who was never going to be America’s sweetheart. There was always something aloof about the man — he radiated folksy charm, but he also came across as a bit distant. When Murray brings him into the audience to shake people’s hands in order for them to get to know him, Letterman doesn’t warm to the suggestion, seeming uncomfortable. (Although understandable, it’s even worse when Murray opens the side stage door and passersby quickly swarm Dave.) For all his strengths, Letterman never had Leno’s effortless personal touch. He didn’t have Carson’s ability to be universal. He wasn’t capable of fully connecting with the mainstream. Those who loved Letterman loved these supposed failings about him. He was always “ours” — he was never everyone’s, because the world was never smart enough to get how great he was.

First nights of new talk shows are famously uneven. The first Late Show with Stephen Colbert was rocky as hell. (Plus, it almost didn’t air because of near-disastrous technical glitches.) Whether it’s a series pilot or a Broadway show, you have to give performers a chance to figure out the damn thing they’re making. The same holds true for Letterman’s first CBS episode — it would get better over time. 

But watching that debut episode again after 30 years, I was also struck by how antiquated this type of talk show is now. From The Daily Show to The Colbert Report to The Eric Andre Show to Desus & Mero to Ziwe to Hot Ones, we’ve now had decades of reinvention of the format, a systematic stripping away of the conventions that Letterman was merely mildly subverting in his day. Plus, there’s none of the viral-y, often gimmick-y moments on that first Late Show that were crucial to later hosts like James Corden. Ensuring people pass a clip around on YouTube — no matter how inane — has become far more important than goofing off and doing nothing.

It’s impossible to believe now, but 30 years ago, Late Show felt like the future of late-night television. And for a while, it was. But it’s a funny thing about the future — it keeps changing as new talents throw out the old and try something fresh. That’s what Letterman was doing back then. In that first CBS episode, he pays tribute to Ed Sullivan’s legacy while also joking about how outdated he was by then-modern standards. It’s both blessing and curse that Letterman has lived long enough and amassed a formidable legacy himself that he now inevitably feels a bit like a relic himself. The greats are always passing the baton on to the next generation — what feels old-fashioned about that first Late Show is the direct result of Letterman’s descendants determined to pay homage to their hero by topping him.

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