Jeffrey R. Staab/CBS
May 20, 2015 04:00 PM

When NBC handed David Letterman Late Night in 1982, his offbeat humor ushered in a new era of late night.

Thirty-three years later, he’s stepping down from a late-night landscape that changed around him, having stayed true to himself as the medium changed from appointment viewing to something to be easily digested the next morning in three- to four-minute clips.

“I recognized the value of it,” Letterman told The New York Times back in April of his competitors’ tendency to gear their shows toward digital audiences. “It’s just, I didn’t know what to say. You go back to your parents’ house, and they still have the rotary phone. It’s a little like that.”

Nevertheless, Letterman, 68, is set to air his last Late Show on Wednesday, leaving behind a legacy as one of the most iconic figures in American media. His candor and prickliness, often seen as points against him, led to some of the most talked-about interviews in late-night history – segments that, in an Internet age, ironically would have easily made him a mainstay in morning-after roundups.

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The David Letterman Show and Late Night with David Letterman

Letterman was a breakout comic from Indianapolis with only an appearance on Mork & Mindy and the good word of Robin Williams to his name when NBC gave him his own morning show, The David Letterman Show, in 1980. Though a critical success, the network was forced to cancel after Letterman’s humor did not mesh with the early-hours audience.

However, NBC had faith in Letterman’s talent and signed him to a contract that would keep him tied to the network, guest-hosting now and then on The Tonight Show Starring Johnny Carson. After Carson was granted the rights to the time slot immediately following his own show, he reached an agreement with Letterman and NBC to launch Late Night with David Letterman in 1982, the first iteration of the franchise.

Johnny Carson’s Retirement, Jay Leno’s Appointment and Late Show with David Letterman

Johnny Carson (left) and David Letterman
Tony Esparza/CBS/Getty

As Carson’s permanent guest host at the time of his 1992 retirement, NBC’s choice to have Jay Leno take over the Tonight Show desk permanently wasn’t without logic. However, Letterman wanted the earlier time slot, and the normally closed-off host made his displeasure quite clear.

Letterman made Leno his direct network competitor in 1993 when he began hosting Late Show with David Letterman on CBS, once again leading the first iteration of a late-night franchise. Conan O’Brien took Letterman’s spot on Late Night.

Carson, too, saw Letterman as his natural successor and even made appearances on Late Show – a courtesy not extended to Leno. Furthermore, as Peter Lassally, an executive producer on Carson who followed Letterman to CBS revealed following Carson’s death, the late Tonight Show host would feed his protégé punch lines for his monologue.

Letterman bested Leno in the ratings for a couple of years, but Leno pulled ahead in 1995 when Hugh Grant made his first public appearance after being arrested by the LAPD for soliciting a prostitute. Leno would go on to maintain that lead for the bulk of his stay on The Tonight Show.

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The Battle Over The Tonight Show, and Its Brief Benefit to Letterman

In one of the biggest public relations disasters in NBC history, the network essentially recreated the dispute that led to Letterman’s departure in the ’90s. This time, in 2010, it was O’Brien who left NBC.

O’Brien was granted Leno’s Tonight Show spot by the network before Leno was ready to retire from late night – and before NBC was truly ready to let him go.

In an effort to keep Leno around, NBC created The Jay Leno Show, which premiered in September 2009 in the 10 p.m. slot. O’Brien experienced a brief ratings bump following his Tonight Show appointment, but it failed to hold the attention of the older demographic that were accustomed to Leno’s older-skewing sense of humor.

Around the same time, Letterman was dealing with his own scandal. In October 2009, the talk-show host copped to having an affair with one of his female staffers after her boyfriend at the time – a former 48 Hours producer – tried to extort Letterman for $2 million in exchange for his silence. Coming from a notoriously tight-lipped man, his on-air apology to wife, Regina Lasko, was a rare peek into his private life.

Over at NBC, the drama continued. When The Jay Leno Show also missed the mark with audiences, NBC became too anxious too quickly and reverted to the status quo in order to quell the rapid dwindling of their late-night audience. In January 2010, the network moved Leno back to 11:35 p.m. and O’Brien to 12:05 a.m., which rightfully angered O’Brien’s fans and the man himself. O’Brien eventually reached a settlement with NBC and he left for TBS, where he now hosts Conan.

The drama and inconsistency over at NBC proved a boon to Letterman, who experienced ratings bumps amongst the kerfuffle. However, it was short-lived – once Leno took back The Tonight Show in March 2010, he eventually took the lead once again.

The Tonight Show with Jimmy Fallon and Letterman’s Retirement

Jimmy Kimmel (left) and Jimmy Fallon
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Jimmy Fallon replaced O’Brien on Late Night and took over The Tonight Show in early 2014 when Leno finally, properly retired from late night.

With Fallon as his direct competitor, Letterman didn’t stand a chance in the ratings. Fallon only compounded a situation that began to gain speed one year prior, in January 2013, when ABC pushed Jimmy Kimmel Live! 25 minutes earlier to the 11:35 p.m. time slot. Both Kimmel and Fallon’s comedic sensibilities, which skewed far younger and which tended to create segments tailor-made for digital audiences, were the final death knell for Late Show.

In April 2014, at the age of 66, Letterman announced his retirement. Given that Letterman had already experienced such a lengthy career, the move was not necessarily influenced by Fallon and Kimmel’s dominance over the late-night ratings. However, the timing was certainly serendipitous for CBS.

“[Fallon and Kimmel] didn’t push me out [of a job],” Letterman told The New York Times. “I’m 68. If I was 38, I’d probably still be wanting to do the show.”

Stephen Colbert, Letterman’s Replacement

Not long after the announcement of Letterman’s retirement, CBS named 51-year-old Stephen Colbert as the newest Late Show host – an appointment for which Letterman was not consulted.

“I thought, well, maybe this will be a good opportunity to put a black person on, and it would be a good opportunity to put a woman on,” Letterman told the Times of CBS’ choice. “Because there are certainly a lot of very funny women that have television shows everywhere.”

While Letterman admitted that he was initially bothered by the slight – “Just as a courtesy, maybe somebody [could have said]: ‘You know, we’re kicking around some names. Do you have any thoughts here?’ ” – he’s the one who “had made the decision [to leave]. This is what comes when you make this decision,” he added.

Colbert is set to officially take over The Late Show on Sept. 8.

David Letterman holding a photo of his son, Harry, who was born Nov. 3, 2003
John Paul Filo/CBS/Getty

As for Letterman’s plans for the future, it seems they will follow much the same path as his mentor, Carson, who essentially disappeared from the public eye following his retirement.

On Thursday, when Letterman awakes to an empty calendar, he intends to spend time with his family and especially with his 11-year-old son, Harry, he told the Times. “For the first time since Harry’s been alive, our summer schedule will not be dictated by me. It will be entirely dictated by what my son wants to do. And I think that’s pretty good.”

Letterman makes his final appearance on CBS’s Late Show Wednesday at 11:35 p.m. ET.

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