Although ostensibly operating in parallel universes, the Venn Diagram between Letterman and “Saturday Night Live” became especially clear during Letterman’s final show, when ten A-List celebrities delivered the “Late Show’s” final Top Ten list. Two (Bill Murray and Tina Fey) were among the most important “SNL” cast members ever; two (Julia Louis-Dreyfus and Chris Rock) were so-so cast members who went on to huge post-“SNL” careers; two (Steve Martin and Alec Baldwin) hosted “SNL” so often they might as well have been cast members; two (Jerry Seinfeld and Jim Carrey) hosted five times between them; one (Peyton Manning) was the single funniest non-comedian ever to host the show; and one (Barbara Walters, aka “Barbara Wawa”) was a constant target of satirical spoofing.
It’s no coincidence that Letterman’s favorite guests were also “SNL” royalty, given the overlapping sensibility of those two shows. The Baby Boomer ethos that “SNL” and Letterman both exemplified was anti-establishment, deeply ironic, absurdist and self-referential. Both shows became so popular because millions of people felt as if Letterman and "SNL" spoke for them.
Letterman famously hailed from Indiana, and “SNL”'s Lorne Michaels was just as famously from Canada -- two of the nicest places in the world -- but “SNL” and “Late Night”/”Late Show” were each hard-core New York City shows, and anything but nice. For 11 years both were produced out of the same building -- 30 Rockefeller Plaza. Even when Letterman moved out, it was to the Ed Sullivan Theatre, only about half a mile away. Both shows actively celebrated the streets of New York, even in its dark days when many tourists were scared to visit; and, of course, both had powerful and emotional episodes after the 9/11 attacks.
It’s hard to remember now since they became such institutions, but the ascendance of “SNL” and Letterman signified a major generational shift following the upheaval of the 1960s. In the blink of an eye, the center of gravity in comedy shifted during the mid-197os from Bob Hope Christmas specials to “Conehead” sketches. Because “SNL” and Lettermen were on so late in those pre-timeshifted days, they would be experienced primarily by younger audiences up past their parents’ bedtimes. They were too popular to be considered cult shows, but definitely outside the frame of reference for the older generation.
What’s surprising in retrospect is that although “SNL” and “Letterman” shared the same DNA, there was little actual affinity between the two shows. Sure, Letterman’s band leader Paul Shaffer was an early performer on “SNL” (and a music director on the “SNL” 40th anniversary show), and Jim Downey, an early “SNL” head writer, was a Letterman head writer for a while. And yes, Joe Piscopo, Norm MacDonald and Jason Sudekis did perform many “SNL” sketches spoofing Letterman; Letterman returned the favor by mimicking Michaels.
But despite the talent overlap, “SNL” and Letterman were like two lions patrolling a common savannah, each feeding on the same wildlife but rarely acknowledging each other and never cooperating. To the best of my knowledge, Letterman himself never came near “SNL’s” studio 8H, and Lorne Michaels never deigned to appear as a guest on Letterman. Presumably they were both too self-important to appear on each other’s shows.
There was clearly a personality disconnect between the uber-cool Michaels and the twitchy, self-lacerating Letterman, a disconnect that certainly worsened in 1998, when Michaels bowed to pressure from his then-boss Don Ohlmeyer and fired Norm MacDonald mid-season. Letterman, never a fan of suits to begin with (especially NBC suits), welcomed MacDonald to his show and proceeded to call “Ohlmeyer” an idiot and refer to Michaels as Lorne “Table-at-Orso's” Michaels.
“SNL” and Letterman didn’t need to cooperate to change comedy, puncture pretense and launch dozens of careers. But it’s possible they stayed too long. Letterman clearly lost interest at the end. I was shocked to hear 30somethings express bewilderment at why his retirement was a big deal. He’d gotten so lackluster and cranky in recent years that he seemed as remote to them as Bob Hope had been to me. “SNL” has similarly lost its urgency in an era of younger comics and more immediate communications platforms.
With Letterman gone, there are few comedic voices left who share his absurdist, edgy humor, although Conan O’Brien comes closest. What’s ascending now in comedy is what Andres du Bouchet, O’Brien’s head writer, calls “prom king comedy.” This is the happy humor of the self-satisfied popular kids (e.g., Jimmy Fallon’s lip-sync contests), rather than the humor of the insecure, which has dominated for the past half-century.
There’s nothing inherently wrong with Fallon’s sunny brand of celebrity-fawning entertainment, as long as it doesn’t crowd everything else out. Fortunately Letterman’s replacement is Stephen Colbert, who was born in 1964 at the very end of the Baby Boom. He’s not as acerbic as Letterman, but he’s equally as absurdist. With luck, Colbert will synthesize the best of Letterman and “SNL” and prove that it’s too early to put Baby Boomer humor out to pasture.