The Naughty Genius of David Letterman, Late Night’s Colossus of Cranky

‘Letterman: The Last Giant of Late Night’ chronicles the host’s journey and legacy. Pulitzer Prize winner Tom Shales on the retired comedian’s greatness.

Photo Illustration by Elizabeth Brockway/The Daily Beast

I had the opportunity, several light years ago, to ask Johnny Carson what he thought of David Letterman, who at that point, early in his career, was widely expected to succeed Carson as host of The Tonight Show on NBC. Johnny looked irked for an instant, then made the gesture for “loony”—one finger doing circles near his head—and said, worriedly yet admiringly, “Lots of ‘stuff’ going on up there,” sounding as if he were Dave’s anxious parent.

That’s an oversimplification but a fairly accurate distillation of what author Jason Zinoman takes more than 300 pages to say in Letterman: The Last Giant of Late Night, just published by HarperCollins. Impressively, the book seems not one word too long and is probably the finest profile ever written of a TV comic, which is praise not meant to be faint. If you even just liked Dave, and especially if you loved him, you’ll get plenty of bang for your book bucks. You’ll be entertained, enlightened (albeit on a subject now culturally remote) and even alarmed at the extent of Letterman’s chronic self-loathing, if that’s really what it was.

Some folks, after all, use self-deprecating remarks to disguise enormous egos, and show business has anything but a shortage of those. Trashing yourself, some theorize, undercuts criticism from others. You may ask, as Zinoman chronicles misery after misery, why poor Dave didn’t seek psychiatric help; he didn’t even reach for antidepressants until fairly late in life. But ironically or not—and irony is a word that pops up very often here, as you’d expect if you’re familiar with Letterman and his three-decade career—curing Dave of his melancholia might also have cured him of his hilarity. It was said of perhaps the most notable media theorist of all time that his genius was linked to a large tumor inside his brain.

We’ll never know. And, sadly, generations alive and unborn may never even get an accurate reading on Letterman’s brilliance, because unlike almost everything else ever seen on TV, Letterman’s work is now largely inaccessible. The electronic ghost of Johnny Carson still quips nightly about such forgotten topics as David Stockman on Carson reruns (over an invaluable cable channel) but Dave, who actually logged more late-night years than Johnny, is nowhere to be found, except maybe as a couch occupant on a Carson rerun.

It’s a fairly safe bet that Letterman could make a regular scheduling of Dave Redux possible but just doesn’t want to, as would be consistent with his mad haunted bitterness. Not all his shows would stand the test of time but in what seems a permanently existential world, that test may no longer be relevant anyway. The test of what?! Why even wonder what time it is, what year it is, what time period it is, when you’re swimming in a quandary of reordered tele-time and trying to figure out which war it is, which recession it is, and which Republicans are screwing what up. It’s a losing battle, and the blasted internet makes it even more so.

There are some facts about Letterman that could be considered timeless, and one of them is that no quicker, smarter or sharper ad-libber ever yammered into a microphone. Zinoman makes the case, generously and intelligently, that credit for the best of Letterman’s shows must be shared among a small army of writers, producers and performers who rode a wavelength to glory, but Letterman was no empty shell propped up by the tireless efforts of others. Zinoman may go too far in spreading the credit around, because Letterman captained that ship but also had it custom-built for him. His sensibility, his ironic detachment or whatever you (or Zinoman) want to call it, suffused the enterprise.

Clearly a young man who (refreshingly) loves and even respects television, Zinoman acknowledges that TV isn’t a performance medium, nor a director’s medium, nor a writer’s or producer’s medium—but rather a chameleonic medium whose identity is in continuous flux. Hal Gurnee, who’d directed Jack Paar’s late-night and prime-time shows years earlier, was also Dave’s director during his arguably most creative, clever time; Gurnee would get extra laughs out of comedy bits by cutting to just the right shot at just the right moment. On the other hand, probably no one contributed more to the comic identity and delirious impudence of Letterman’s NBC show than the great Merrill Markoe, for years his head writer and bosom, uh, buddy. Or just plain bosom.

Zinoman celebrates and appreciates many of Letterman’s antic trademarks, one of them his delight in language, in word play, and in unearthing old words and phrases seemingly retired. It may sound trifling, but we hadn’t heard “lovely” used so frequently, especially by a man, in many a year—a “lovely” piece of pie, a “lovely” evening in the theater, whatever. These word revivals seemed not like affectations and did not make Letterman sound quaint; they were part of his peculiar individuality, part of his stubborn love affair with the language, and could be utterly disarming. He could also, of course, sharpen words to a fine point and use them as weapons. They were part of what made Dave Dave.

Other parts were not so endearing, and Zinoman dutifully covers painful events of Letterman’s life that were lived under the harsh spotlight of television, none more disappointing than his confession of having had affairs with members of his staff, an admission prompted by one miffed Romeo’s attempt to blackmail Letterman over an affair with one particularly attractive young woman. Letterman hit his audience with that one quite unexpectedly one night. Part of the soliloquy was Letterman reassuring disbelievers, “Yes, I do have sex”; many of his female fans apparently considered Dave to be hot stuff.

Yes, really.

Zinoman takes note of a venerable broadcast tradition that goes back to radio: populating a series with a cast of characters who regularly brighten. This was especially true of Letterman’s early late years, when he materialized in the seeming safety zone on the other side of midnight, but stayed true when he moved to CBS and an earlier slot. If you’re a true Letterman loyalist, just hearing or seeing such names as Mujibur and Sirajul will make you smile; they were two Bangladeshi merchants who set up shop on Broadway near the Ed Sullivan Theater, home to Letterman’s CBS Late Show.

Others live on in memory, or moved on to other gigs even if they hadn’t been “professionals” until Letterman staff discovered them. None was more of an innocent than Larry “Bud” Melman, a part-time anchor and civil servant who had to revert to his real name, Calvert de Forest, when Letterman moved from NBC to CBS (NBC claimed Larry “Bud” Melman as the network’s “intellectual property”). There was a night when Letterman’s Late Show dispatched Melman to the Port Authority Bus Terminal to welcome travelers arriving in the city on buses when a simple gag ascended to wonderment that had even Letterman helpless with laughter back in the studio.

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Less naïve but every bit as malleable was Rupert Jee, who operated the tiny Hello Deli around the corner from the theater. Here the joke was not merry incompetence but, in part, Jee’s willingness to be Dave’s Fool, to go along with any gag that seemed to amuse the studio audience. That crowd—tourists, New Yorkers, deadbeats and drifters—was another of Dave’s props, and if they weren’t responding to the material, Dave could be despondent beyond reason. Beyond Reason was his realm.

Dave’s mother, Dorothy Mengering, was also drafted into the cast; she died only last week, at 95, back home again in Indiana. In the course of their conversations for the book, Zinoman got Letterman to talk about his father, Harry Letterman, a subject that Dave had avoided in most other interviews. Harry Letterman, a florist who had a brief flirtation with show business, died in 1973, and Dorothy remarried.

Most important of the performing contributors during the formative years of Letterman’s television show had to be Chris Elliott, son of the great deadpan satirist Bob Elliott who was half of the comedy team of Bob & Ray (Goulding). Elliott talked Letterman into some of the riskiest, nuttiest business ever done on the show. I met Elliott, and got to have lunch with him and his father, during those formative years. I asked Chris why Dave had seemed chilly after our first encounters; Elliott theorized, “He was probably afraid you wanted to be his friend.” Oh.

I also enjoyed, wildly, a lunch that Dave set up with Jack Paar at the 21 Club in Manhattan, Dave’s gesture of homage to one of his television icons. I was invited along because I knew Jack (a critic can be friends with TV stars of yesteryear). Revealingly if trivially, Dave chose a table in the basement of 21, definitively nothing fancy, while Jack later complained to me that he wished we’d been up on the splashy top floor where celebrities are more readily recognized. Dave even had an NBC limo sent to suburban Connecticut to bring Jack (and wife Miriam, who went shopping) into the city.

I didn’t know just how historic the lunch was. Back in the office, for years thereafter, staff members were absolutely incredulous at the idea of Dave going out to lunch and behaving even to that degree like a celebrity. I wasn’t trying to psychoanalyze Dave in those days, or ever, but Zinoman does a bang-up job of it. “For his whole life, Letterman maintained a ferocious fear of failure,” Zinoman writes, “but that didn’t mean success made him happy.” On the same theme, the best of Letterman’s succession of producers, Robert “Morty” Morton, put his finger on the show’s decline in adventurousness after moving from a funky NBC studio to the grandiose Ed Sullivan Theater: “In the old show, we always celebrated failure. Now we celebrated success.”

Dave had a passive-aggressive management (to stretch a term) style that drove the staff(s) crazy, and remained impenetrable pretty much to the end. “Nothing he hates more than direct conflict,” says no less an authority than Jeff Lewis, who’d been one of Dave’s fraternity brothers at Ball State University back home again in Indiana (I’m going to keep quoting lyrics from that state song until forced to stop).

Whether Dave was at his best when his show was riding high in the ratings, or if dreading failure actually made him funnier (somewhat, but only somewhat, the way Carson’s monologue struggles could be sublimely hilarious) is one of a million unanswered questions to be saved perhaps for some other book. Or will there be other books? Zinoman subtitles his book “The Last Giant of Late Night,” which is apt partly because “late night” itself seems to be all but gone, a “time slot” rendered obsolete by the vagaries of the infernal internet. To his credit, Letterman never became a Dot-Commie. His most faithful fans will remember him struggling with a keyboard at his desk as he attempted to send a single piece of one-sentence email. And failed.

Coincidentally or not, Dave never stooped to telling a studio audience to “give it up for” the next guest to walk out. Not to his credit, Dave sucked up to such guests of dubious value as Bill O’Reilly and Rush Limbaugh, slipping in sly remarks but basically flattering them with a respect they hardly deserved. Tom Brokaw is no demagogue; he’s a justifiably respected newsman who came up with a humdinger of a label for his parents: The Greatest Generation. Why, though, did Dave always introduce Brokaw as if he were Ed Murrow, David Brinkley and William Randolph Hearst rolled into one? He was on safer ground flirting playfully with beautiful actresses, though some will wonder how playful the flirtations really were.

Having affected a long, ugly white beard in recent months, Letterman has been quoted as saying that the more people complain about it, the more securely it stays fastened to his face. Still the naughty child, though it’s not as endearing now that there’s another kid in the house, one far more entitled to behave like a brat. Enfants terribles can be sad when they reach their seventies, or is that the moment when they most deserve to pop balloons and pull pigtails, a last hurrah in the schoolyard?

What’s most clear from reading Zinoman’s painstaking study: Dave probably got a better biographer than he deserved. I laughed out loud, and delightedly, but only during the parts of the book that dealt with Letterman’s helter-skelter NBC late-night show, when Markoe called many of the shots and Letterman seemed so strikingly fresh and smart-alecky, and cameras were strapped onto monkeys and dogs or hoisted into the rafters.

Guy Lombardo—now there’s a memory-tester even for Greatest Generationists and Boomers alike—joked once on an NBC comedy show that “when I go, I’m taking New Year’s Eve with me.” See, his band specialized in “Auld Lang Syne.” Oh never mind—except that when Dave Letterman left, he took “late night” television with him. I didn’t think I’d miss him, but Letterman has proven me wrong, and I’m grateful.