Moving from earning minimum wage to making millions, Jay Leno's life is anything but boring. The automotive aficionado made a name for himself in show business on The Tonight Show, which he hosted for 22 years, reportedly earning up to $30 million per year.

Despite being in the public eye for over three decades, there are tons of things many don't know about Jay Leno. Like the fact that he doesn't drink alcohol or that he doesn't own any shorts. Jay has had some not-so-proud moments in his career that many fans don't know about and that's what we will dive into now.

Related: 10 Cool Cars Jay Leno Wishes He Owned

9 He Tried To Get The "Tonight Show" Job From David Letterman

Leno might be the hardest working man in show business, but he's also the most hated man for many reasons. One of which is because he spent a better part of the late '80s trying to cozy up to Carson's older viewers on The Tonight Show while he was still on cool terms with Letterman, who was supposed to be Carson's replacement.

Leno played his cards right and was eventually named as Carson's successor but before he managed to get the job officially, Letterman succeeded in changing the minds of the NBC executives. Unable to back down, Leno launched a PR campaign that gave him the opportunity of interviewing and speaking to affiliates and advertisers on the show in a bid to garner their support.

8 He Spied On NBC Executives

Long before Leno disguised into an NBC press conference, he had another underhanded thing, which goes way back to 1992, when he eavesdropped on a conference call involving NBC executives. Jay hid in a closet and listened to NBC executives deliberating on who's better suited to host The Tonight Show between him and David Letterman.

Leno not only listened but took notes of the conversation. Up until 2014 when Jay confirmed the story himself, it was just a rumor. In the interview with Access Hollywood, Leno claimed that he didn't have a manager or an agent, so he needed to know what was going on behind his back.

Related: 14 Things You Didn't Know About Jay Leno And His Cars

7 He Can't Master The McLaren P1

Whether it's the latest supercars or the oldest muscle cars, Jay Leno's garage got them all. However, there's just one car Jay confessed he can never learn the ropes, and that's the McLaren P1. In a tour of his garage with automotive YouTuber Shmee150, Leno admits he's not a racecar driver, and so he's not good enough to master every trick up the McLaren P1's sleeve.

The McLaren P1 is a feat of engineering and a work of art at the same time. Its 3.8-liter V8 engine is complemented by a 131 KWh electric motor for a total output of 903 hp. The P1 boasts a 0-62 mph time of 2.8 seconds and a top speed of 217 mph.

6 His Failed TV Show

In the fall of 2009, Time described Jay Leno as "the future of television." But it wasn't because of his entertaining attributes, but simply because he was cheap. Running the Jay Leno Show every day of the week would be cheaper than running an hour-long primetime drama.

The show failed due to dismal viewership, as advertising rates plummeted by over 70%. Just four months after its premiere on September 14, 2009, NBC's Jay Leno Show was axed.

5 His Manager Planted Fake News About Johnny Carson

After Jay Leno was announced as The Tonight Show host upon Johnny Carson's retirement, he had to just stick around until Carson finally left the show. But Leno's manager Helen Kushnick is not exactly the most patient person in the world, so she planted a fake story in The Post in a bid to get rid of Carson.

The hit piece on Carson, which was about NBC executives' supposed disappointment with Carson's performance was published on February 11, 1991, but Leno claimed the story didn't come from his camp, which Carson never believed anyway.

Related: What People Don't Know About Jay Leno's Car Collection

4 He Hates Ferrari's Customer Treatment

For someone who owns around 180 cars, you'd expect one or two Ferraris to be in his collection, but hardcore automotive enthusiast has never actually bought one for himself. That's not to say Jay Leno hates Ferrari vehicles, because he doesn't at all. He has actually driven several Prancing Horses including the Ferrari 275 GTB4, Ferrari 288 GTO, and most recently the 2021 SF90.

Speaking on Jason Stein's podcast, Cars, and Culture, Jay Leno opens up on his decision to steer clear of Ferraris, even though they build cool machines. Leno's dislike for Ferrari has to do with the dealership and customer experience. He says they require customers to have purchased other Ferraris before they can get access to an exclusive model.

3 His Feud With Arsenio Hall

Jay Leno is hated by many celebrities including Arsenio Hall, who is perhaps his most vocal opponent and their feud dates back to the early '90s. Speaking with Good Morning America, Hall says his issue with Jay Leno is based on his willful blindness to his Machiavellian behavior.

Leno and Hall used to be friends, but enmity started brewing when Leno started cutting into Hall’s territory by inviting guests like Eddie Murphy, the Black Crowes, and Simply Red – the kind of guests that usually appear on The Arsenio Hall Show.

2 His Anti-Asian Jokes

The media and entertainment world is becoming increasingly vocal about anti-Asian hate and violence. But Jay Leno has more than a decade-long history of anti-Asian jokes, which he finally apologized for last year.

Leno's apology comes after several years of campaigning by the Media Action Network for Asian Americans (MANAA), a group focused on the advocacy for positive coverage and portrayals of Asian Americans in the media. Leno says at the time, he thought the jokes were harmless.

1 His Obesity Rants

The thing with comedy is that it's sometimes difficult to know when your joke crosses the line from being funny to being offensive. In 2019, Jay Leno appearing as a guest on The Tonight Show now hosted by Jimmy Fallon is seen ranting about obesity.

According to the Obesity Action Coalition (OAC), Leno's joke was not only stigmatizing but also "offensive on many levels". The group issued a statement asking Jay Leno to tender a public apology and for that particular episode of the show to be taken down.