Preface

This article is the first in a two-part series. In this two-part blog series, I will cover in depth the two major conflicts in the history of The Tonight Show, starting with the 1992 conflict between David Letterman and Jay Leno, which occurred after Johnny Carson’s retirement from the show. Next week’s article will be about the infamous 2010 conflict between Jay Leno and Conan O’Brien. This week’s article will serve as a prologue of sorts, providing context for the climate that contributed to the Conan O’Brien situation in 2010. Now, I want to preface this two-part series by admitting that I do have a bias. I am a fan of both David Letterman and Conan O’Brien. I am not a fan of Jay Leno, but I respect and acknowledge his place in comedy history, especially his early years as a stand-up comedian. My goal with these articles is not to slander Leno, and I will try not to let my bias show. I also want to make it clear that all the blame for these two conflicts cannot be placed solely on Leno, as NBC’s historically toxic corporate culture contributed significantly to these infamous television debacles. These two conflicts have been the subject of two books from New York Times writer Bill Carter: 1994’s “The Late Shift,” which chronicles Leno and Letterman’s competition for The Tonight Show, and “The War for Late Night,” which chronicles the conflict between Leno and Conan. “The Late Shift” was also adapted into an HBO film that is available to stream on HBO Max.

Leno and Letterman

The Tonight Show is the most prestigious comedy show of all time. Since its first broadcast in 1954, The Tonight Show has had six permanent hosts: Steve Allen, Jack Paar, Johnny Carson, Jay Leno, Conan O’Brien, and Jimmy Fallon. Johnny Carson is widely regarded as the greatest late-night talk show host of all time and hosted The Tonight Show for thirty years. In 1982, David Letterman launched Late Night with David Letterman, airing every night at 12:30 after Carson. Letterman’s hosting style differed significantly from Carson’s, and Letterman leaned into the surreal and absurd with a humorously dismissive attitude toward his role as talk show host. These factors led to Letterman becoming a massive hit with younger audiences, and to Johnny Carson having great respect for Letterman despite their different styles. If you would like to learn more about David Letterman and Late Night, you can read about him in a previous article I wrote, linked here. Jay Leno was a very successful stand-up comedian who was in the same comedy club circuit as Letterman early on in both of their careers. Jay Leno was not only a very successful stand-up but also recognized by his peers, including David Letterman, as a great comedian, earning the reputation as a “comedian’s comedian.” His guest appearances on Carson and Letterman’s shows were always a big hit, and those appearances, along with the fact that he was based in Los Angeles, helped earn him the guest host role for The Tonight Show. Leno’s skill as a comedian and entertainer cannot be understated. 

In 1990, Johnny Carson had been the permanent host of The Tonight Show for nearly thirty years. Carson remains a beloved figure in the history of comedy and late-night television, and while he was still immensely popular, he was older, and the possibility of his retirement seemed imminent. At the time, Jay Leno served as the permanent guest host for the show, filling in for Carson, who regularly took at least one night off each week. David Letterman had been hosting Late Night every night at 12:30, after The Tonight Show, since 1982, and it was widely believed that Carson’s replacement would be Letterman. One person who feared Letterman would succeed Carson was Helen Kushnick, Jay Leno’s agent. Helen Kushnick may be one of the most consequential people in the history of late-night television, and the tactics she used to secure The Tonight Show for Jay Leno are a perfect reflection of just how sneaky and conniving television network politics can be. She started buying ads in papers and running fake stories about NBC looking to fire Johnny Carson. She then negotiated a deal with the NBC executives, guaranteeing that Leno would get the show after Carson’s retirement despite the fact that Carson had not yet publicly expressed any plans for retirement. Leno insists to this day that he had no knowledge of Kushnick’s activities. He even went so far as to call Johnny Carson himself and tell him he had no knowledge of anything, and there have been conflicting reports since as to whether Carson believed him. Johnny Carson announced his retirement in 1991, with Kushnick’s fake stories being a contributing factor to Carson’s decision to retire. NBC subsequently announced Leno as his replacement, a move that shocked and disappointed many, including Johnny Carson. Letterman was disappointed, angry, and heartbroken. Carson’s final show as host of The Tonight Show aired May 22, 1992, and a new era of late-night television began.

Jay Leno’s tenure at 11:30 had a rocky start, with many critics and audiences comparing him unfavorably to Carson, and with Helen Kushnick meddling in production. Kushnick brought her fierce, combative tactics to her new role as executive producer of Leno’s Tonight Show. She would urge guests to cancel appearances on other talk shows, including Arsenio Hall and Letterman. She would even threaten to ban guests who did not cancel their appearances elsewhere. She repeatedly clashed with the same NBC executives who secured the show for Leno, which made them increasingly displeased with her. Meanwhile, Letterman, who was still hosting Late Night at 12:30, had teamed up with legendary Hollywood agent Michael Ovitz and was seeking a deal for a new show. Tensions between Kushnick and the network reached a breaking point, with discussions of firing Leno and giving the show to Letterman even taking place. Leno grew increasingly paranoid about his fate on the Tonight Show. So much so that he actually hid inside a broom closet in the NBC affiliate offices so he could eavesdrop on the executives’ discussion about him and Letterman. Yes, that really happened. Eventually, Leno was given an option. Either fire Kushnick from her position as executive producer of The Tonight Show or risk being replaced. Now, Jay Leno had been working with Kushnick for years and owed his entire career to her. Their connection was so strong, in fact, that he even promised her dying husband that he would always take care of her. Leno has always prided himself on his loyalty and his word. He fired Kushnick immediately and continued to host The Tonight Show. 

After months of behind-the-scenes tension and indecision among NBC executives, Leno remained the host of The Tonight Show, and David Letterman was offered a deal by CBS to host The Late Show weeknights at 11:30, competing with Leno. Letterman’s replacement at 12:30 was Conan O’Brien, a then-unknown writer for The Simpsons who had previously worked as a writer for Saturday Night Live. It was an unconventional choice at the time, and Conan initially struggled to find his footing, but he has since become another late-night legend. Letterman and Leno’s friendship never recovered, but both have expressed mutual respect for each other in the years since. Both Jay Leno and David Letterman have retired from their respective shows. Since retirement, Leno has continued to tour the country performing stand-up comedy. David Letterman has hosted his talk show, My Next Guest Needs No Introduction, on Netflix since 2018. Since his retirement, Letterman has left a rich legacy in comedy, with his absurdist style influencing many comedians and talk show hosts. Leno’s reputation took a minor hit during this time, especially after the publication of Carter’s book and the subsequent HBO film, leading many to see Leno as sniveling and insincere. However, despite Helen Kushnick’s shady behavior, Leno earned his spot as host of The Tonight Show fair and square. His reputation would take a significantly bigger hit in 2010 during his conflict with Conan O’Brien, which will be covered in next week’s article.