The greatest minds of future generations will someday ponder a pair of towering questions of late-20th/early 21st-century history.
Why Jay? Why not Dave? Was that Jimmy Kimmel or a test pattern with legs? (Bonus question.)
Sadly, you're stuck with the most questionable minds of this generation—those belonging to television critics—for obsessive analysis of this engrossing issue.
As a New York-based critic during the early-'90s battle for the Crown of Carson between Leno, Letterman, Arsenio "I'll Kick Jay's Ass" Hall and (you can't see it, but I'm laughing uncontrollably and in danger of wetting myself at the memory) Chevy Chase, I was privileged to witness all the breathtaking pettiness, conducting several interviews with Leno and attending rare Letterman press conferences.
Winnowing the field to the two that mattered, Leno and Letterman split the stylistic difference of the semi-deified Carson, whose vox-populi persona was that of a nice Midwesterner streaked with naughtiness. Leno grabbed the nice, rooted it in mass-market sensibilities and sold it to Middle America. Letterman co-opted the naughty, anchored it in the winking irony of the coasts and tickled Urban America.
Vast generalizations, certainly, with plentiful overlap on each side, but the prevailing wisdom nonetheless.
As history reminds us, Letterman clobbered Leno in the opening salvo of their battle to emerge as America's leading night-light for late-night nookie. Until July 11, 1995, when Hugh Grant sheepishly visited the Tonight couch to mutter a mea culpa over being Divined (long before Bill was Lewinskyed). Leno deftly condensed America's tittering curiosity by asking Grant, "What in the hell were you thinking?"
Since then, America, as measured by Nielsen, hasn't wavered in its preference for the Burbank clown over the Manhattan cynic. To which critics have since been asking America, What in the hell are you thinking?
This despite overwhelming press bias toward Letterman, whose relationship with reporters is a dysfunctional dance. With his cranky (and intriguing) aloofness, Letterman's like the hot babe who aggressively avoids you—making you even hornier for her. And Letterman's ironic distance is a love-match for cynical critics. Leno, conversely, is exceedingly chatty around any rolling camera, running tape recorder or open notepad within quoting distance. To the press, he's the homely chick who wants you waaaaaay too much.
Very "high school," isn't it?
Letterman gets the glam-love, the passion of the sophisticates. Letterman wins Emmys. Letterman is named to funniest-people lists. Leno is dissed. Leno doesn't win Emmys. Leno is pointedly left off funniest-people lists.
Letterman is credited with leading the country back to laughter after 9/11. Leno is called the "least distinguished host" in Tonight Show history by USA Today.
How painful can Leno's Tonight get? Ever seeen his "Jaywalking" segments, when Leno interviews John & Jane Q. Public on the street, feeding them easy common-knowledge questions so they can give (or fake) goofy answers for our so-called amusement? 'Nuff said on that. In more than a decade, his interview skills have advanced from awful to tolerable. Only his monologue—laden with annoyingly repetitive riffs—is fairly reliable and provocative.
Letterman continues to sparkle, getting funnier as he grows crankier. His biting Late Show monologues, challenging interviews, eyebrow-arching 'tude, top-10 lists and bountiful bits—especially at the expense of our president and California's beefy governor—are ever-relevant treasures.
And Leno gets more viewers. Nightly. Roughly six mil for Leno, four mil for Letterman, with Leno maintaining a healthy advantage among 18-49-year-old viewers by whom ageist nets and advertisers declare victory. Yet even with a recent contract extension and annual pay hike from a reported $17 million to $27 million, Jay still earns less than Dave's rumored $33 million.
I broke ranks from many of my critical colleagues in late August 1993, predicting the about-to-bow Letterman would win the sprint—curiosity was rampant and here was a retooled Letterman for America to sample, while Leno had been a late-night fixture since assuming Carson's chair in May 1992—but that Tonight would claim many more tomorrows in the ultimate race.
As a seasoned crank and devoted cynic myself, I relate to much of the Letterman dyspepsia, especially his eternal distrust of the three and a half C's: Convention, Conformity and Corporate culture. But as witty—far wittier than Leno at his wittiest—and affable as he's capable of being, as admirable as his stubborn independence may be, Letterman inevitably reveals the disaffected misanthrope at his core.
Which is why Leno's mastery over the masses makes perfect sense. He's what I've spent a lifetime praying never to become personally, while acknowledging that it's the surest path to what you want to become professionally.
He plays the game, plays it with conviction. And his work ethic is the star-spangled American model that resonates with the red, white and blue majority, handing the edge to the Big Chin over the Gap-Toothed Grin.
Leno's labeled a corporate suck-up, cozying up to Peacock affiliates and playing network emissary/mascot/sycophant at galas to seduce advertisers and critics. He'll poke fun at bosses, but never wantonly attack them. Corporate suck-up to some. Obedient employee to others. So are most Americans. Bitch and mock though we may, we carry The Man's water. It's how the country works.
Leno genuinely digs the gig. The man actually giggles through nearly every Tonight Show. Letterman seems to disdain his audience. Lurking just beneath those spiffy double-breasted suits is the sense that we're fools for watching him. His dour irony fascinates the minority and the media, but most Americans are still a sincere lot, and Leno is sincerely in love with his job.
Though considerably richer than the rest of us, Leno is the hardworking employee most Americans see in themselves. Works 300 days a year, never takes sick days—the night he didn't appear, he swapped jobs with diva of the dawn, Katie Couric—even banks his entire Tonight salary, living off his continuing standup career. Absurd as it sounds, he's planning for retirement, like any blue-collar wage slave.
Letterman, though a noted perfectionist and control freak when it comes to every detail of The Late Show, tends to whine over his workload; takes time off (beyond extended absences for heart surgery and a tussle with shingles) and turns the show over to guest hosts; and muses about hanging it up early. He's the office malcontent with little to be discontented about.
As America watches obscenely wealthy athletes and entertainers renegotiate contracts and stage holdouts, Leno acknowledges his insane paycheck. "Millionaires arguing at midnight!" he joked when the late-night wars erupted. And after accepting NBC's "very generous" raise: "I'm still not making Dave money, but I don't need the money. If you can't live on what I make, there's something wrong with you."
When Leno lagged behind Letterman in the early '90s, he eschewed excuses, crediting Letterman's creativity. But after dropping behind, Letterman slimed then-pitiful CBS, blaming the network's loser lineup and lack of lead-in power. Today, backed by a re-energized CBS and potent lead-ins, Letterman remains a loser to Leno.
Leno "brands" his Tonight Show, appearing as himself in a fistful of movies (outdone only by non-late-night attention hog Larry King), a practice Letterman mostly shuns.
Ironically, Letterman's evolution into a slick showman might signal a man out of sync with a medium that, owing to reality TV, is growing more aggressively proletariat. As "regular folk" assume the face of television, the nattering, fumble-prone Leno seems the cozier fit on the broader landscape of the medium.
Leno's most criticized traits—hammering home punch lines and beating one-liners to within an inch of their effectiveness—render him similar, and strangely endearing, to anyone who oversells a joke at the office or over a beer. His sloppy sense of humor is our sloppy sense of humor.
Columnists lambasted Leno for seeping into political advocacy by embracing California Gov. Arnold Schwarzenegger—The Governator announced his candidacy on Tonight (a coup Letterman would have given his gap teeth for) and Leno introduced him at his victory party—while stroking Letterman for his "equal-opportunity" barbs. They got it wrong. Leno recognized that Schwarzenegger—and the entire recall election—was such a belly flop into farce that defied partisan politics that by latching onto it, he'd strike a gusher of comedy. Substitute Alec Baldwin for Arnold and you'd still get Leno as comic exploiter.
Conversely, Letterman's relentless comic pounding of Dubya—granted, the prez is one of the juiciest targets in decades—has the sting of an agenda, his (always hilarious) taped bits reaching beyond the monologue zingers his idol, Carson, made iconic at the expense of numerous chief execs. LA Weekly last week reverently called Letterman "the hands-down leader when it comes to unabashed Bush-bashing." It lends him the aura of a blue-state mouthpiece more than Leno's rap as a red-state toady.
Jay Leno will never enjoy Carsonian lionization or Lettermanesque respect.
He simply connects with America, this week from Las Vegas.
And if I've saved the greatest minds of future generations valuable time and effort, so they can move onto more crucial historical queries, such as whatever happened to Justin Guarini?
Glad to do it.