When Jay Leno stepped out from behind the curtain for the first time after taking over The Tonight Show, he was nearly pushed back by the applause. The longtime stand-up comedian had established himself after multiple late-night appearances and gigs filling in for the host he would ultimately replace, Johnny Carson. And although he was welcomed by an enthusiastic audience that night, Leno, at least with a joking humility, showed an awareness of how public opinion can turn over time.

“Let’s see how you feel in 30 years,” he told the crowd. Now, almost three decades later, Leno has moved past the bitter late-night wars in which he was tangled and is regularly touring as a stand-up. After all this time, Leno can’t say he’s changed much. He won’t say the same for everyone else.

“Being on the road is the best grounding experience. Because when you live in Hollywood, especially when you have something like The Tonight Show, people laugh at stuff that’s not funny,” says Leno.

When it comes to comedy, Leno draws a line between the typical Tonight Show monologue and the material he tries out on the road. While late-night hosts rely on hyper-topical punchlines best-suited for rehashing around the office water cooler, a ticket-buying audience expects a little more. For Leno, this means expressing himself more personally — something he says has become a bit more of a minefield.

“The weird thing about it is we live at a time where if people don’t like an entertainer’s politics, they don’t like what it is they do. I came up in the era where you just made fun of both sides, and people drew their own conclusions as to where you stood on an issue,” says Leno. “My favorite week is whenever I hear from somebody, ‘Well, Mr. Leno, you and your Republican friends, I hope you’re very happy.’ Then later I hear, ‘You and your Democratic buddies, I watched the show.’ Then I know I’m doing a good job because everybody is equally angry.”

Mention Leno’s first stand-up appearance on The Tonight Show in 1977, and he’ll respond with a self-deprecating “I’m sorry about that.” But mixed in with his jokes about the weather was a sharp observation from the rising comedian well before he began appearing in living rooms across the country five nights a week.

Mocking the clichéd expressions that spilled from the mouths of local news anchors, Leno leveled with the crowd, “Let’s face it. Nothing shocks us anymore. They should just tell the truth. [Slipping into a booming impersonation of a TV newsman] ‘World came to an end today. Most Americans couldn’t give a damn about the whole thing. Give me a hamburger and some gasoline.'”

This understanding of the general public would inform how Leno connected with his audiences for years to come. As he explains, “I found very quickly doing The Tonight Show, once you get past secretary of state, nobody knew who the hell you were talking about … It’s the reason more people watch the People’s Court than watch the Supreme Court.”

In addition to his time as a touring comedian, Leno also hosts Jay Leno’s Garage. Alternating between the more technical episodes that are published on YouTube and the Emmy-winning series on CNBC, the show features Leno in his element, sharing his passion for automobiles. According to Leno, his hosting duties on the show are a bit more in his comfort zone compared to The Tonight Show, which would often involve him feigning interest in a guest’s athletic accomplishments (Leno’s not a big sports guy) or humoring the star of the latest cinematic misstep.

Of course, no discussion with Jay Leno is complete without bringing up his 1998 WCW tag-team match that pitted the comedian and in-ring partner Diamond Dallas Page against Eric Bischoff and Hollywood Hulk Hogan. To prepare for his debut in the squared circle, which Leno says raised around $100,000 for charity, the late-night host practiced his moves for six weeks every evening after taping The Tonight Show. Although Leno remains one of the few TV personalities to claim a victory over the Hulkster, he sometimes has to contend with fans unable to separate him from his brief in-ring persona.

“To this day, people come up to me and go, ‘Look, I know wrestling is fake, but I knew you were really mad when you went after him,'” says Leno, who always fails to dissuade others as to his true feelings toward Hulk Hogan.

In a way, this particular brand of fandom is no different from those who try to impose their own opinions on the comedian and former late-night host. Almost 30 years after he first claimed his seat at The Tonight Show desk and went on to be cast as the antagonist to fellow late-night hosts David Letterman and Conan O’Brien, Leno says the biggest change is that attention spans have gotten shorter. Meanwhile those jumping to their own conclusions, whether in person or online, are able to cover more distance than ever before.

“Everybody brings their own preconceived notions. To this day, people tell me, ‘I know Obama had you fired from The Tonight Show because you did some jokes about him.’ No, Obama didn’t. TV is a business. They couldn’t care what your politics are, one way or the other — unless it intrudes on the income of the show,” says Leno. “But this kind of talk, this is the worst part of the internet. It’s very funny. It’s just another variation of the Hulk Hogan thing.”