"When you work in show business, you get paid stupid money for silly things," says Jay Leno, the former host of NBC's The Tonight Show (1992-2009, 2010-2014), Television Hall of Fame inductee and recipient of the Kennedy Center's Mark Twain Prize for American Humor (both in 2014), as we sit down to record an episode of The Hollywood Reporter's 'Awards Chatter' podcast. We're meeting in Leno's office within one of several cavernous warehouses near the Hollywood Burbank Airport where he houses and maintains 160 cars and 130 motorcycles and shoots the show that he now hosts, CNBC's Jay Leno’s Garage. Its profile and audience are a fraction of those possessed by the iconic late-night franchise over which the 67-year-old presided for 23 years, but it has brought him just as many Emmys — he won for outstanding variety, music or comedy series for The Tonight Show in 1995 and outstanding short-format nonfiction program for Jay Leno’s Garage in 2011 — and seems to give him every bit as much satisfaction. "The heart works best when the hands and the head work together," he says with a smile that juts out what may be the most recognizable chin of all time.

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Leno was born in New Rochelle, New York to an insurance salesman father and melancholic housewife mother, and he grew up in Andover, Massachusetts. trying to make his mom laugh. He overcame his dyslexia enough to attend Emerson College in Boston, where he developed his interest in comedy (he loved the work of Robert Klein) by venturing into standup (in jazz clubs, strip clubs, retirement homes, mental hospitals and prisons). After graduating, he moved to New York City and continued to perform, but, not long after an unsuccessful audition for Saturday Night Live, he decided to relocate to Los Angeles. "The comedy scene was out here, Johnny Carson had just moved to California, all the shows were out here — I thought, 'Well, this seems to be the place to be.'"

Things in L.A. weren't immediately wonderful for Leno — he briefly was homeless and was picked up by police for vagrancy on several occasions — but once he won stage time at The Comedy Store he quickly made a name for himself. He and another young comedian there, contemporary David Letterman, became mutual admirers and friends. "Letterman was very awkward as a performer — kind of shuffling and looking at the ground — but a brilliant wordsmith," Leno recalls. "I went up to him and I said, 'Oh, man, you really use words well.' And he goes, 'Well, I was watching you. How can you be so confident on stage?' So we sort of took a little bit from each other at that point." Leno soon began landing spots on The Tonight Show with Johnny Carson and The Merv Griffin Show. Letterman, meanwhile, was the first to land a TV show of his own, Late Night with David Letterman, in the 1980s, and Leno was a frequent guest.

From 1987 through 1991, Leno served as the main substitute for Carson, and then, when Carson announced that he would be stepping down in 1992, NBC offered Leno the job of replacing him and becoming The Tonight Show's fourth host, after Steve Allen, Jack Paar and Carson. This was a blow to Letterman, whose lifelong dream had been to host the program. "Johnny was always very nice to me, but I think it's fairly well known that Johnny wanted Dave," Leno notes, "But Dave had a tough relationship with the network." Leno adds, "Of course, somehow I got this moniker of being this horrible person," ostensibly for "stealing" the job from Letterman, when in fact Leno had been the only person other than Carson in the host seat for years. Further complicating matters, Leno's Tonight Show got off to a poor start and there was talk that he might be replaced by Letterman — some reports suggest that Letterman even received an offer, but pride led him to CBS, where, from 1993 through 2015, he became Leno's chief competitor.

Leno managed to right the ship of The Tonight Show by 1995 — a set-change, a highly watched interview with Hugh Grant and his take on the O.J. Simpson case all helped — and he held on to first place in the ratings ever after. Despite grousing from some critics that he had "sold out" and no longer was the edgy comedian they had fallen in love with before he got the show, he proved a reliably genial presence and played well with middle-America, reading as warmer than Letterman — he shook hands with audience members at the beginning of each show, interacted with the public on the street with his "Jaywalking" segments, generally avoided politics and spent his off days performing standup all across the country. "I was a standup comedian who was lucky enough to get a talk show," he says. "Letterman was a broadcaster who didn't really like being a standup comedian."

In 2004, despite remaining atop the ratings, Leno says he was informed by NBC that they had crafted an exit plan for him, whereby Conan O'Brien, who long had hosted the show after Leno's and with whom Leno says he "used to be great friends," would succeed him as host of The Tonight Show five years later. "I didn't know all this was going on behind my back," Leno says. "They told me about it after it was done." He elaborates, "I mean, they came in and they said, 'Listen, you're out and Conan's in." Leno feels that the network was angling for a younger host who might attract younger viewers and would have forced him to depart sooner had he not had a "pay and play contract," explaining, "They had to keep me. They would have just gotten rid of me at the time — 'Here's your money!'"

But by the time 2009 arrived, Leno still was at number one and was not yet ready to retire. He could have left The Peacock Network for a competitor, but he says that would have meant unemployment for many of his decadeslong employees — plus, with his ratings still strong, NBC did not want him to wind up going head-to-head with O'Brien. They reached a compromise: NBC offered him a prime-time show that would lead in to O'Brien's Tonight Show, and he accepted. "I let myself get talked into it," he confesses. "I thought it was stupid at the time. Anyway, the show didn't work. Okay, fine. But meanwhile, I think The Tonight Show was not doing well either. I mean, you can blame it on the lead-in, but everybody gets bad lead-ins — I mean, that's why they hire you, to make up for a bad lead-in. But somehow this was my fault."

NBC, trying to salvage the situation, proposed moving Leno's show later into the night and pushing O'Brien's start time back, as well, to which Leno was amenable, but O'Brien was not. "And then Conan quit," Leno says, marking the beginning of a public feud in which Leno again was portrayed as a conniver. "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?" Regardless, Leno stepped back into his old job in 2010, and points out, "When we came back on, we were number one again, just like that, and we stayed number one until we left and I handed it over to Jimmy [Fallon in 2015]."

Tensions between Leno and Letterman continued right through the end of their respective runs. Letterman was invited but refused to participate in Leno’s final episode and vice-versa. "I asked David first," Leno says. "You know, David is odd — he's just awkward. I just think it would have been really awkward for him. 'Just something on tape? Leno who? Anything?' He said, 'Nah, I'm just not comfortable. That's your night. I don't wanna do it.' We may have talked over the phone. But he just was not comfortable with it. You know, anybody that knows Dave knows he's quirky, if not— To me, it was always quirkiness; it was never meanness." Leno was surprised when, after his request was spurned by Letterman, Letterman's team made the same ask of him: "I said, 'Well, I kinda feel like Dave. You know, Dave didn't do mine and it worked out fine, so, I mean, I think it looks like I'm trying too hard.'"

Leno insists that he doesn't miss hosting The Tonight Show or the drama that came with doing so. "I was lucky," he says. "I did it at a time when Bush was dumb and Clinton was horny." Now, he says, things have gotten much darker. "I don't like Trump, I can't stand the guy, I don't like him personally. But the constant negative Trump stuff on a nightly basis? I think it has a debilitating effect on people. People are just, 'Oh, gosh, I don't wanna watch TV anymore. This is just the same thing every night.'" These days, the man who once was paid $30 million a year to tell jokes in front of millions on a nightly basis finds similar satisfaction in talking about cars — sometimes with fellow celebrities, other times with full-time mechanics — in front of a much smaller audience once a week. Jay Leno's Garage began as a non-commercial YouTube venture in 2006, but it proved so popular that CNBC commissioned a special broadcast of it in August 2014 and then began airing it as a weekly primetime series in 2015. Over the years, it has accumulated seven Emmy noms for outstanding short-format nonfiction program, winning once.

Leno has been a "car guy" for almost all of his life — he worked as a mechanic during college and always has found acquiring and restoring cars to be therapeutic, in a way. "See, comedy's subjective," he explains. "Some people think you suck, some people think you're funny — they're both right. I mean, they're both correct, you can't argue with that. But if something is broken — if an engine was not working, and now it runs — well, no one can say it's not running. 'Okay, look, see it's running. It's working now.' It's a definitive answer. You can't really get a straight answer in show business." Moreover, he says, working with cars helps him to keep him grounded. "When you take a transmission out of a car, and your hand's all cut up and the fluid's burning your hand, and you realize some guy makes $80 for that — and then you go over and talk and you get thousands of dollars. So it just puts things in perspective."

The third CNBC season of Jay Leno's Garage debuts June 28, with an episode that was shot at George W. Bush's Texas ranch. Even though Leno says the 43rd president is more of "a truck guy" than a car guy, they had plenty to talk about, as Leno finds to be the case with anyone even remotely interested in automobiles. "The fascinating thing about automotive history is it's only about 150 years old," he says. "I mean, if you're studying Egyptology or something like that, you've got to go back tens of thousands of years, whereas with this you only have to go back to the guy who lived before your grandfather, and maybe some of those people are still around or some of those stories are. Most of the artifacts still exist, most of the history is reasonably fresh, so it makes it sort of interesting."