What Happened to David Letterman?

Last Updated on June 26, 2024

It’s October 2009, and Woody Harrelson has a zombie comedy to promote. But before he can do so on THE LATE SHOW, David Letterman has something to share. And so, after his monologue, Letterman took to his desk, telling those in the Ed Sullivan Theater that he had a story to share. No top 10 lists. No stupid pet tricks. No visits with Rupert Jee at the Hello Deli. For 10 minutes, Letterman laid it out. One morning, he woke up to find an envelope in the back seat of his car, and in it was proof that he had been having affairs with members of his female staff. This was as raw and stripped as David Letterman had ever allowed himself to be in decades on late-night television. And it wasn’t Jay Leno or Les Moonves or any of his foes that caused it. It was David Letterman himself. But did this destroy his career and reputation? Was he able to bounce back?

There are more than 10 reasons we chose our subject this week…So let’s find out: WTF Happened to…DAVID LETTERMAN?

But to truly understand what the fuck happened to David Letterman, we go back to the beginning. The beginning began when he was born on April 12th, 1947, in Indianapolis, Indiana, most notably born to Dorothy, a frequent staple around Mother’s Day and Thanksgiving of his later programs.

Letterman proudly attended Ball State University, taking to communications…and quickly being fired from the public radio station, a touch too radical for their taste. But Letterman would press on, earning a spot as an Indiana weatherman…with an unorthodox approach, once congratulating a tropical storm on being upgraded to a hurricane. He would also serve as host of a children’s show and a late-night movie showcase, wherein he took to blowing up replicas of the station building. As he built his reputation in small venues such as this, David Letterman was making a play for stardom.

And so off to Los Angeles he went (the Indiana entertainment industry isn’t exactly booming), doing standup at the famed Comedy Store and failing an audition for Ted Striker in AIRPLANE!, which he admitted was for the better. But these – and MORK & MINDY one-offs – wouldn’t suffice; fortunately, he soon made his first appearance on THE TONIGHT SHOW in 1978, with legendary host Johnny Carson taking to the irreverent wit immediately. Letterman would go on to appear and serve as guest host dozens of times throughout the 1980s. And it was Carson’s home station, NBC, that snagged Dave, giving him a morning slot with THE DAVID LETTERMAN SHOW in 1980. It would only last five months but it nabbed him a pair of Emmys.

In 1982, Letterman earned LATE NIGHT WITH DAVID LETTERMAN for NBC back in New York, positioning himself as “the rightful successor” to Carson over the course of nearly 2,000 episodes. It was here that Letterman perfected his style, packed with snark, stunts and schtick, delivering nightly Top 10 lists, frequent Stupid Pet/Human tricks and occasional bits with the Monkey Cam (yes, a camera strapped to a monkey’s head), suits covered in Alka-Seltzer/Velcro/magnets, and whatever other surreal material he wanted on the air. One major segment came in its debut year, when absurdist performance artist Andy Kaufman was slapped by pro wrestler Jerry Lawler, an immediate highlight reel moment which blurred the lines of not only fact and fiction but the limits of television. There was an undeniable artistry to it all. This wasn’t your father’s late-night show – it was your stoner roommate’s. And for it, he was passed over.

In 1992, after much turmoil behind the scenes and with Johnny Carson retiring, THE TONIGHT SHOW was given to Jay Leno – despite Carson naming Letterman “the rightful successor” to the late-night show (he would even send Letterman jokes for his monologue later on, showing where his loyalty always was). Instead, Letterman headed for CBS at the Ed Sullivan Theater, landing THE LATE SHOW and further making his mark on the late-night scene, transforming it for a new generation.

For its run, THE LATE SHOW – and Letterman – were in direct and constant competition with THE TONIGHT SHOW and Leno, with the Chin always edging out his late-night nemesis in the ratings. But Letterman’s popularity persisted, proving to be the true underdog of the format. While the American public as a whole preferred Jay, the industry – and a certain cult following – seemed to have more respect for Dave, and in 1994, he and his show won their first Emmy for Outstanding Variety Series, beating Leno to the punch. THE LATE SHOW would go on to win six total, the most of any traditional late-night talk show in history. But the bitter resentment – as overblown as it would become (how many feuds become fodder for a TV movie?) – has evidently been squashed, with the two pairing up for a 2010 Super Bowl ad…along with Oprah Winfrey, another foil of Letterman’s.

At the height of his fame, David Letterman hosted the 67th Academy Awards in 1995 (no, CABIN BOY was not nominated, although we love Dave, aka Earl Hofert as Old Salt in Fishing Village), giving a go that many considered one of the worst attempts at hosting in the ceremony’s history (see: “Uma, Oprah. Oprah, Uma.”). He would later say, “It took me less time to get over the bypass surgery than it did to get over hosting the Academy Awards.” That surgery came in 2000, marking a dramatic turning point for Letterman, who admitted it made him more vulnerable and susceptible to erupting in tears. But his acerbic humor remained, even petitioning to have a road named the David Letterman Bypass in Indianapolis. When he returns to the LATE SHOW, he is met by Foo Fighters’ “Everlong”. They would play the same song during the show’s final episode.

In the audience for that last show, which aired on May 20th, 2015, were Letterman’s wife, Regina, and son, Harry. Loyal she was, having been the victim of an extramarital affair that had gotten so public – stemming from blackmail/extortion attempt by a CBS producer – that Letterman was forced to confront and address it on the air in 2009, admitting he had cheated, with one lover outed as assistant/intern Stephanie Birkitt, who often appeared on the show, often called by dumb nicknames for a willing intern that was now pet names for a lover. He had been outed as a scumbag and a cheat. In the aftermath, Letterman would retrospectively be criticized for his on-air treatment of women: leering, commenting on looks, and throwing a “gotcha” style that promoted gossip at the likes of Lindsay Lohan and Paris Hilton.

And yet, during his 10-minute monologue on October 1st, 2009 – in which he outlined the scope of the blackmail plot and confirmed he had affairs with employees – the live audience met him in the middle with applause and laughter. It was as if it was no surprise, just par for the course for Letterman, late-night television’s underdog. (The Birkitt scandal had just been the latest controversy surrounding Letterman, who had had numerous run-ins with stalkers, one even committing suicide in 1998. Letterman – and his son Harry, born in 2003 when his old man was 56 – was also part of an attempted kidnapping plot in 2005.)

It was a storied career on late-night TV indeed, filled with highlights and lowlights at his desk, with career-defining moments that hit every spectrum of the medium: Madonna cursing at him, Crispin Glover nearly kicking his head off, Drew Barrymore flashing him for his birthday, cornering/humiliating fragile female celebs, giving Michael Richards the chance to apologize (a failure), mocking Sarah Palin’s daughter for her teenage pregnancy, welcoming American audiences back after 9/11, letting us in on her fragilities, and so much more. But after 6,000 episodes and 33 years, THE LATE SHOW was done. But David Letterman was not. His fans knew he wouldn’t really retire and hole up in a Montana cabin. And by 2018 (two years after being honored at the Peabody Awards), he was signed with Netflix, launching MY NEXT GUEST NEEDS NO INTRODUCTION, interviewing everybody from Kim Kardashian to Ukrainian president Volodymyr Zelensky. It’s the perfect transition for David Letterman. He had matured; it was all still there – the humor, the curiosity, the honesty – but the playing field was different.

So, too, was late-night television. Consider the following names: Fallon, Kimmel, Corden, Meyers, Colbert (his successor) – none of them have what Letterman did. Who cares about doing karaoke with your guests, or what does the internet tweet about them? Or lip-sync battles? Late-night television is just so safe now, so obsessed with the viral moment, so afraid to flip the bird to the network or call out the suit in charge. When David Letterman “retired”, he not only ended one of the greatest TV shows of all time, he also took with him the late-night renegade.

We think of one of David Letterman’s finest interviews and one of the greatest displays of his humanity: that with Warren Zevon, in which the musician, less than one year from death, offered the following advice: “Enjoy every sandwich.” And might we add: Toss every object in sight off the fucking roof. How fitting as a literal and metaphorical embodiment of everything David Letterman was at his peak.