NEW YORK (TheStreet) -- David Letterman long understood the ridiculousness of celebrity, and pulled few punches with his guests. Even Oprah Winfrey.
It's a quality that remains an essential part of his charm. Letterman's jabs at serial narcissists and thin-skinned movie stars rankled their handlers and overpaid publicists, but it endeared the Indiana native to folks smart enough to appreciate that celebrity is at best a fleeting notion.
Letterman announced Thursday that he will leave the set of CBS's (CBS) Late Night sometime in 2015. At 66, after three decades in late-night television, Letterman has apparently decided it's time to do something else.
Though he was born in the Midwest and keenly proud of his roots, Letterman has always been an East Coast kind of guy. His infamous foray into the lion's den of the Academy Awards' annual dog-and-pony show in 1994 is one of dark legend. Letterman couldn't resist the temptation to poke fun at Hollywood's insulated, self-congratulatory world. "Oprah, Uma, Uma, Oprah." Oil and water. The academy never asked him back.
Letterman's priorities were elsewhere. He revered Johnny Carson, and appreciated what that other Midwesterner did for comedy as well as the art of the interview. Over his 30 years in late-night television, Letterman has made no secret of his admiration for comics such as Bill Cosby, Richard Pryor, Rodney Dangerfield and Don Rickles, another comedian unafraid to tweak the rich and the pretentious.
There was a time when everyone who watched television knew Rickles, and Letterman is nothing if not an historian of his craft.
Letterman's decision to call it quits fits in with his consistent determination to decide the parameters of his show, and if possible, when and where it would air.
It came as no surprise in 1992, when Letterman made clear to his employers at General Electric's (GE) NBC that he wasn't about to spend a lifetime seated behind Jay Leno. Letterman was unafraid to use his Late Night seat to poke fun at executives of GE, a global industrial corporation, for attempting to run a television network. Jay Leno wouldn't dare go over that line.
Letterman had seemed a shoe-in to takeover for Carson, who had announced his decision to leave the Tonight Show in May 1991. So, when NBC chose Leno rather than Letterman to succeed Carson, Letterman took his act and longtime bandleader Paul Shaffer of Thunder Bay, Ontario to CBS.
And CBS couldn't have been happier. CBS CEO Leslie Moonves and the company's shareholders have benefited handsomely from Letterman as a consistent source of revenue. Letterman may not have always won the ratings war with Leno, but there was certainly enough revenue to boost the company's stock price. In retrospect, the move to CBS was the right one. The Tonight Show has consistently skewed older while Letterman's humor was most fervently based in younger audiences and city dwellers more apt to revel in the acerbic.
Back when I was in college, Letterman was in something of a competition with Arsenio Hall. Some people actually thought Hall's antics were anything but juvenile and that somehow Hall would win out in that ratings battle. But Hall was all about pandering to celebrity and his show is now long forgotten.
I finally got to see a Letterman show a year ago, having won a silent auction at my daughter's school. Bittersweet, the lead guest that night was Regis Philbin, not exactly my first choice. But in retrospect, Letterman's banter with Philbin revealed his loyalty to the comedy family, to a man who most people knew as host of a morning show but Letterman knew from watching TV in the late-1960s from a couch in Indianapolis.
It also happened to be the night that New York City mayoral candidate Anthony Weiner revealed himself as Carlos Danger. Letterman wasted no time with that present.
Many of his writers -- Conan O'Brien, Chris Elliott -- went on to larger careers, while many comedians -- Garry Shandling, Jimmy Kimmel -- were heavily influenced by Letterman.
Letterman could be prickly, and in 30 years he made some enemies, but more than anything, he remade the role of the television talk host. Just to be included among a list with Carson, Steve Allen, Jack Paar and even Jay Leno, has to make the former Indiana weatherman more proud than he's willing to let on.
On the day after Letterman announced his departure from Late Night, shares of CBS were falling 1.5% to $61.41.
--Leon Lazaroff is TheStreet's deputy managing editor.
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