He played hard. He played smart. And, by many accounts, he was funnier than the other guy.
But when David Letterman leaves late-night TV after his final show Wednesday night, he will leave as an also-ran. No matter how much moral outrage his defenders can muster - no matter how many column inches were filled by writers who said America should like him more - Letterman is the man who couldn't beat Jay Leno, and sometimes couldn't beat Leno's replacement.
"He was a former weatherman and a failed morning-show host who perfected a sort of snide, irreverent attitude towards showbiz types," Rolling Stone wrote after Letterman announced his retirement last year. "After getting noticed by Johnny Carson and making a fan out of NBC bigwig Fred Silverman, however, David Letterman found himself taking his goofy antics to a 12.30 am time slot - and thus, a late-night TV legend was born."
There was no doubt that the legend was, well, legendary. Letterman feuded with Madonna, tried to engage a nearly mute Joaquin Phoenix and avoided getting in between Andy Kaufman and Jerry Lawler. He invented the "Top 10 list"; he invented "Stupid Pet Tricks"; he poked a hole in the absurd, celebrity-fuelled gas bag that was late-night television.
But there's this thing about legends: They usually come out on top. Abraham Lincoln didn't lose the Civil War; BB King didn't step down as the ambassador of blues. Letterman's panache - his unbridled impertinence - wasn't enough. People admire the New York Yankees, but not because they lost to the Boston Red Sox in the 2004 American League Championship Series.
Perhaps a sense of "shoulda-coulda-woulda" is why Letterman seemed a bit at sea in a recent New York Times look back.
"I'm awash in melancholia," he told the paper of Wednesday's exit. "Over the weekend, I was talking to my son, and I said, 'Harry, we've done like over 6,000 shows.' And he said, (high-pitched child's voice) 'That's creepy.' And I thought, well, in a way, he's right. It is creepy."
"It is creepy": Not exactly the note any showman should want to go out with while comparing retirement to "a good, solid punch to the head." Contrast this to Leno's first act after he retired the first time: He stole back his own show from Conan O'Brien and, after his second retirement, won a Mark Twain prize and leaped back on to the stand-up comedy circuit.
Letterman need not look to Leno to see what spunk looks like, of course. He just needs to look at the 1993 news conference in which he announced his move to CBS. The weatherman from Indiana could have been worried about the big jump to 11.30 pm ET on a new network. Instead, he joked about Amy Fisher before getting down to business.
"As some of you may know," Letterman said, "in the past year and a half, I've kinda been interested in doing a show earlier than the one I'm doing now." Ever the smart aleck, he thanked CBS for its "patience," "support" and, slyly, "generosity." (Letterman's three-year deal was worth $42 million.)
David Letterman, right, and guest Bill Murray in the 80s. Photo / AP
For a while after that news conference, Letterman was riding high. He beat Leno in the ratings for a few years; an HBO film portrayed Leno as a bit of a lunk. But then Leno interviewed Hugh Grant on July 10, 1995, beating Letterman for the first time. Leno held on to the lead for much of the next two decades.
Thus began Letterman's very long, very public tenure as second banana.
"We prevailed for a while, and then I lost my way a little bit," Letterman told the Times. "Quite a little bit. And at that point, there was not much I could do about it. People just liked watching his show more than they liked watching my show."
Sounds brutal. Some said it didn't make a difference: Letterman was loved less than Leno, but loved by those that mattered.
Watch: The best of Letterman's 'Top 10 List'
"As Leno prepares for his final few Tonight shows, he finds himself in a unique position: More widely watched than any of his competitors, yet widely reviled by the majority of his peers," EW wrote last year.
So what? After all, Letterman's shtick did not always play well - his attempt at hosting the Academy Awards ended in disaster, for example. And after he suffered personal setbacks, he retreated from the snark that had made him famous. He took a hiatus for a quintuple bypass in 2000, then brought his doctors on-air to thank them for saving his life. And he fessed up to an extramarital affair in 2009.
"I want to be the person I always thought I was and probably was pretending I was," he told Oprah Winfrey in 2013. "I hurt a lot of people. ... I'm not looking to blame anybody. I'm looking to find out why I behaved the way I behaved."
This was the guy who pioneered "Will It Float?"
People assemble outside the Ed Sullivan Theater in New York during the final taping of The Late Show. Photo / AP
"Now he's more of the Old Softy," The Washington Post's Hank Stuever wrote. "Maybe it was the heart surgery."
When not gushing with gratitude or regret, Letterman could seem petty. Even as the host reached out to Leno for a 2010 Superbowl commercial, he was taking O'Brien's side in the Leno-O'Brien wars.
As Corinne Heller of ABC 7 in Los Angeles explained: "I was delighted by everything that happened - except you losing your job," Letterman told O'Brien on The Late Show in a May 2012 interview, during which both TV hosts did a mock imitation of Leno."
If Letterman wanted to use a 20-year-old feud for laughs or simply remind his audience the feud existed, such comments seemed irrelevant. Late night was already moving on.
"Today's late-night talk shows - viral-culture enterprises comprised of buzz moments and component parts that can be embedded, downloaded, tweeted - are produced with tonight, tomorrow, or anytime audiences in mind," EW wrote last year. "Letterman helped develop this game too. But he, like Leno, doesn't play it/never played it as well or with as much interest as his successors."
