Jay Leno has long been considered an everyman, albeit an everyman with millions of dollars in the bank and a fleet of cars hidden in a Burbank aircraft hangar. Stories about Jay Leno and his insatiable desire to host The Tonight Show are legendary in comedy circles, and despite being written about at length in Bill Carter’s books The Late Shift and The War for Late Night, many people aren’t aware of Leno’s do-anything-to-win attitude.

Leno pulled maneuvers that sound like something out of an NBC drama rather than the behind-the-scenes antics of a talk show. You may know Leno and Letterman had a falling out over who would host The Tonight Show in 1992, but what suggests Jay Leno is a jerk are the stories of how he rose to prominence as the voice of Middle America in the early ’90s. Even though Leno claims to be an unassuming guy who just ended up in show business, he reportedly employed underhanded tactics to create a toxic atmosphere in which he thrived.

Long before Late Night Wars of ’92 began, people were sure David Letterman was the next in line to host The Tonight Show. Not only was Letterman hosting The Late Show – the program that followed Johnny Carson’s show at 11:30 pm – but he openly glorified the gig. In a 1989 interview with Time, Letterman was already fielding questions about taking over for the beloved host. When asked if he would take over for Carson when he retired, Letterman answered, “I guess, of course, I would. But I think ultimately I would be happy just to be considered.”

If only Letterman knew how wrong he was, and if only he knew he – and the hosting gig – was in Jay Leno’s crosshairs.

He Wore A Disguise To An NBC Press Conference So He Could Ask Questions About Himself

Photo: CNBC

In 2008, before Conan O’Brien took over The Tonight Show, Jay Leno was in high-stress mode because he was being pushed into retirement. Since there weren’t any critical conferences for Leno to eavesdrop on from a closet (which he did in 1992), he opted for a different espionage strategy.

Donning a bald cap, glasses, and shaggy goatee, Leno went to an NBC press conference and managed to ask NBC Universal co-chairman Marc Graboff a couple of questions about himself. First, he asked when Leno’s last show was, which broke the news. And in his most telling moment, he asked, “Now, Brett Favre retired and then wanted to come back, and the Packers said no. What do you make of that?”

Graboff told the in-disguise Leno that NBC wouldn’t be allowing the star to return saying that it “puts management in an impossible situation.”

Jay Leno Spent Years Trying To Get The ‘Tonight Show’ Job From Letterman

Photo: NBC

Leno’s campaign of passive aggression began long before Johnny Carson announced his plan to retire from The Tonight Show. Based off the strength of Leno’s rapport with his then-friend David Letterman on The Late Show, Leno was able to sign on as the permanent guest host of The Tonight Show in 1986.

Throughout the late ’80s, Leno was able to ingratiate himself with Carson’s older viewers, while still playing it cool with Letterman. According to people who worked on Carson’s staff, Leno was never openly vying for the job, but Letterman could feel The Tonight Show slipping away from him every time Leno filled in as host.

As time went on, Leno worked everyone in NBC and managed to get named as Carson’s successor. But he didn’t have the job just yet. At the same time Leno was glad-handing, Letterman had retained the services of Michael Ovtiz – the co-founder of Creative Artists Agency (CAA) – who managed to get NBC to change their mind about Leno.

Leno didn’t let this get him down, though. He began a grassroots PR campaign that saw him giving interviews to anyone who would have him and speaking directly to affiliates and advertisers in order to garner their support.

Leno’s Manager Planted A Fake News Story Attacking Johnny Carson

Photo: NBC

After Leno signed on as the host who would take over for Johnny Carson after his retirement, he had to sit around while Carson figured out when he would leave the show. Leno’s manager, Helen Kushnick, became impatient and decided to plant a fake story about NBC being disappointed with Carson’s performance.

An anonymous “associate” told The New York Times: “[Kushnick] asked me to plant a story somewhere,” with no attribution, saying NBC execs thought Carson was stale and his audience was too old. The story ran in The Post on Feb, 11, 1991 with the headline: “There Goes Johnny; NBC Looking to Dump Carson for Jay Leno.”

Leno claimed he didn’t know who concocted the story, and that he was sure it didn’t come from his camp. When he told Carson this, the host simply responded by saying, “It came from you.”

Jay Leno Hid In A Closet To Spy On NBC Executives

Photo: NBC

One of the more underhanded things Leno did to ensure he became host of The Tonight Show was to eavesdrop on a conference call while hiding in a closet. According to Bill Carter’s The War for Late Night, in 1992, Leno hid in the closet of an empty NBC office and listened as executives discussed whether he or Letterman should host The Tonight Show.

Leno listened in and took notes about who was on his side, as well as who wanted Letterman to take the job. This story was just a rumor until a 2014 Access Hollywood interview with Leno where he copped to the whole thing:

I was in, there’s a huge closet in there. I just pulled the door behind me and listened, very simple. I didn’t have an agent, I didn’t have a manager, I don’t have anybody. It’s nice to know what’s going on.

Leno’s assertion that he didn’t have an agent was in direct opposition to a 1992 Entertainment Weekly article that noted Leno had been using the services of manager Helen Kushnick since 1975.

Leno’s Booking Staff Pushed Dennis Miller Out Of Late Night

Photo: NBC

David Letterman wasn’t the only late night host dealing with the brunt of Jay Leno’s passive-aggressive actions. In the early ’90s, Leno did everything he could to make sure smaller late night hosts like Dennis Miller and Arsenio Hall lost out on guests, though he and his team claim they never tried to lure guests away from smaller shows.

After Dennis Miller’s foray into the world of late night failed in 1992, he told Entertainment Weekly:

The booking wars exist, that’s all I can say. For [Leno’s team] to say it doesn’t exist – well, I was privy to the whole schematic. It exists in spades.

 

Leno And Arsenio Hall Went Head To Head

The most vocal of Leno’s opponents in the early ’90s was Arsenio Hall, and he never pulled his punches. He told Good Morning America that his anger with Leno stemmed from the host of The Tonight Show being willfully obtuse about his Machiavellian behavior:

Jay and I used to be friends. Dennis and Jay used to be friends. Johnny handed over a legacy, and they never mentioned each other’s names. Something’s wrong with someone who is always surprised about people being upset with him.

When Leno was asked by an audience member what he thought about Hall’s anger with him, he seemed to shrug it off by saying, “Hey, welcome to show business! What are you gonna do?”

He Waged His Most Long-Lasting And Acrimonious War Against Conan O’Brien

Photo: NBC

Twelve years after the “Late Night Wars” came to an end, a new battle was brewing. Conan O’Brien, who had been dutifully hosting Late Night since Letterman’s departure, was due to host The Tonight Show, but Leno wasn’t ready to give up the reigns. In Bill Carter’s The War for Late Night, the biographer claims Leno signed what was then referred to as his last contract extension in 2004.

He put on a nice face for the NBC execs, but when he spoke to the people who were closest to him, he said it felt like NBC was breaking up with him. He may have not yet hatched the plan to usurp O’Brien, but Leno was figuring out a way to keep working. He even went so far as to secretly promise his staff that if he had to, he would take a deal at ABC and move the show to their Disney lot.

After Agreeing To Step Down, Leno Decided He Wanted His Show Back From O’Brien

Photo: NBC

After agreeing to step down from The Tonight Show in 2009, Leno didn’t exactly disappear. Instead, he became like a ghost haunting an ancient castle. To appease Leno, NBC CEO Jeff Zucker gave him The Jay Leno Show, a 60-minute comedy variety show at 10 pm that was basically like The Tonight Show, but without the celebrity interviews.

The show debuted to massive ratings, but the 18 million viewers dwindled quickly, and NBC was left scratching their heads. At the same time, O’Brien wasn’t drawing huge ratings on The Tonight Show at 11:35, so NBC decided to cut The Jay Leno Show down to 30 minutes, move the show to the 11:35 time slot, and push The Tonight Show to 12:05. O’Brien was furious, writing in an open letter:

…NBC executives told me they intended to move the “Tonight Show” to 12:05 to accommodate the “Jay Leno Show” at 11:35. For 60 years, the “Tonight Show” has aired immediately following the late local news. I sincerely believe that delaying the “Tonight Show” into the next day to accommodate another comedy program will seriously damage what I consider to be the greatest franchise in the history of broadcasting. The “Tonight Show” at 12:05 simply isn’t the “Tonight Show.”

O’Brien quit and, needing a host for The Tonight Show, NBC turned to a familiar face: Leno.

He Tried To Rehab His Image On ‘Oprah’ – Except He Wouldn’t Admit To Any Wrongdoing

Photo: CBS

After everything was said and done, Leno had The Tonight Show back, and O’Brien was off the air for seven months until the non-compete clause of his contract with NBC ended. Viewers rightfully thought Leno had acted like a megalomaniac, so he did what everyone does when they need to rehabilitate their image – he appeared on Oprah.

In the interview, he claimed the whole thing had nothing to do with his posturing and that he was brought back to The Tonight Show because of ratings. He did, however, admit to telling a “white lie” in 2004 when he promised O’Brien he would get The Tonight Show.

He explained to Oprah, “I told a white lie on the air. It was just maybe easier that way.” Leno claims he told the lie because he thought he would have a new job by the time O’Brien took over as host.

Leno Doesn’t Think He Did Anything Wrong, And Has Never Apologized For His Behavior

Photo: NBC

To paraphrase Conan O’Brien, there’s a “very clean story” inside Jay Leno’s head where the longtime Tonight Show host is the hero of the Late Night Wars. Leno has never admitted wrongdoing beyond telling a “white lie” to O’Brien. He continues to state it was O’Brien’s poor ratings which lead NBC to return the show to Leno, and that it would have been ridiculous to refuse to take back the show when it was offered.

As for his culpability, Leno believes his hands are clean:

I sort of smile when I read about how I “conspired” – you know, “Jay Leno demanded the show back and they had to give it to him because they had to pay him $150 million.” No, they didn’t have to give me $150 million. I mean, if I’m that smart, how did I lose the show in the first place?

 

Leno Played Jimmy Kimmel – But Kimmel Got The Last Laugh

Photo: ABC

Jimmy Kimmel has remained very open about getting played by Jay Leno. Not only does Kimmel say he was sympathetic to both Letterman and O’Brien in their respective feuds with Leno, he claims that during discussions of a move from NBC to ABC (as The Jay Leno Show was bombing), Leno instigated a friendship with Kimmel.

Leno noted that if he were to move to ABC, he would be bumping Kimmel’s time slot – something he allegedly didn’t want to do. The two had many conversations concerning the move, but as soon as Leno decided to stay at NBC, those conversations ended. To Kimmel, it seemed like Leno was just befriending him in case something happened. As soon as he was no longer needed as a potential safety net, he’d run out of use to Leno.

This false friendship resulted in Kimmel appearing on The Jay Leno Show in the midst of the Late Night Wars to, in theory, support Leno. But in a live-to-tape segment where Kimmel was asked about the best prank he ever pulled. Kimmel responded:

I think the best prank I ever pulled was, I told a guy once, “Five years from now, I’m going to give you my show.” And then when the five years came, I gave it to him and I took it back, almost instantly.

It didn’t stop there, as four more simple questions followed, all of which Kimmel used to work in a dig at Leno and his treatment of O’Brien. All Leno could do was uncomfortably laugh along.

Pretty Much Everyone Hates Him

Photo: NBC

If you need any more proof that people flat out don’t like Jay Leno, here’s what many of the former talk show host’s peers have said about him:

  • Prior to beginning work on his ABC talk show, Jimmy Kimmel told TV Guide he planned on doing “the comedy version of The Tonight Show.”
  • George Lopez called Leno “the biggest two-faced dude in TV” and “the worst interviewer on TV.”
  • Howard Stern noted, “I’ve never seen anybody who behaves like a robot like this guy. Where’s the emotion? Where’s the humanity?”
  • Chris Rock said, “You’re a bad man, Jay Leno” to the host’s face when he was a guest on Leno’s program following the O’Brien kerfuffle.
  • Patton Oswalt compared Leno to disgraced president Richard Nixon: “There’s a Rick Perlstein book called Nixonland… the kind of rise of Nixon, and his sort of drive to power, is weirdly parallel with Jay’s, I think.”
  • After Dennis Miller lost his late night show in 1992, he told Entertainment Weekly, ”Jay and I were very good friends at one point. I don’t think I’d talk to him again, nor would he want to talk to me.”
  • Arsenio Hall described Jay Leno as “punk-ass Leno” in regard to Miller’s cancelation.