There are two sides to Jay Leno. There's the poor kid that worked two jobs. In his teenage years, he started performing stand-up comedy and his life went in a new direction. He quickly became one of the most talked-about comics in the world. In the 90s, he became the host of The Tonight Show. Numerous comedians dreamed of getting that job, but it was Leno who ended up as the host. Leno served as host of the iconic show from 1992 to 2009, and again from 2010 to 2014. To some people, Leno is the beloved Tonight Show host that made America laugh every night.

However, there's another side of Jay Leno. He was at the center of two high-profile controversies involving The Tonight Show. He showed a ruthless side; he would do whatever it took to get what he wanted. He's been in celebrity feuds as well. In fact, Leno's been at the center of several controversies. At the same time, he won't let anything stand in the way of him making millions. Leno's made wild statements and claims, which put him back under an intense spotlight.

It's time to take a closer look at Jay Leno. He's 20 Sketchy Things About Jay Leno Everyone Chooses To Ignore.

20 The Late Night War Part I: Jay Leno vs. David Letterman

In the early 90s, The Tonight Show host, Johnny Carson, shockingly announced his retirement from the iconic late-night TV show. Suddenly, NBC was on the search for a new host. Most people, including Carson, assumed David Letterman would be Carson's successor.

At the time, Letterman hosted Late Night, which followed Carson on NBC. However, Jay Leno had spent years trying to wrestle the gig away from Letterman. Eventually, this resulted in a The Tonight Show conflict during 1991-1992. Leno ended up with the job, and Letterman left NBC with very bitter feelings.

19 Leno’s Controversial America’s Got Talent Joke

Jay Leno no longer hosts The Tonight Show. However, he remains a prominent figure in television. Of course, he's still stirring up controversy.  Recently, Leno appeared as a guest judge on America's Got Talent. He made a controversial joke, which NBC edited out. The joke was deemed racist and offended many people involved with the show. Several Asian-American groups demanded NBC cut ties with Leno.

18 The Late Night War Part II: Jay Leno vs. Conan O’Brien

After years of hosting The Tonight Show, Jay Leno decided he wanted to avoid the situation with David Letterman in the early 90s. In 2004, Leno declared he would retire in 2010 and would pass the torch to Conan O'Brien, who hosted Late Night at the time. However, that was his public face. Privately, he felt NBC was trying to "break up" with him. Rumors suggest he began hatching a plan to get his show back.

17 Howard Stern And Jay Leno 

Jay Leno has a tough time avoiding celebrity feuds. For some reason, he's always upsetting some celeb. For instance, Howard Stern and Jay Leno have been enemies for years.

For the record, Leno doesn't consider Stern an enemy and has never responded to him. Stern criticized Leno for years, including on his radio show and in his memoir, Private Parts. Stern even weighed in during Leno's conflict with Conan O'Brien.

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

In 1991, NBC picked Jay Leno to succeed Johnny Carson as host of the Tonight Show. However, Leno's then-manager, Helen Kushnick, got impatient and wanted to push Carson out. She planted a fake news story that claimed NBC was tired of Carson. Leno claims he had nothing to do with the story. Of course, Carson never believed Leno and always felt the story came from Leno.

15 Jay Leno's Celebrity Feuds

At one point, Jay Leno was one of the most respected comedians amongst his peers. He influenced an entire generation of comedians who grew up watching him. However, Leno's image has dramatically changed over the years. For instance, there's a long list of celebs that don't like him.

George Lopez is a comedian who's made some harsh comments about Leno. Lopez sided with Conan O'Brien during the Leno/O'Brien conflict. Also, another comedian, Patton Oswalt, compared Jay to Nixon and noted Leno isn't the comic he once was.

14 Leno Hid In A Closet To Spy On NBC Executives

Jay Leno will do whatever it takes to get what he wants. He didn't care how ruthless he had to be to steal The Tonight Show from David Letterman. He even hid in a closet once to dig up dirt.

In 1992, Leno hid in a closet and eavesdropped on an NBC conference call. The NBC executives were debating who should host the show, between Leno and Letterman. Leno took notes on who was on his side and who was against him. In 2014, Leno finally admitted to hiding in the closet.

13 The Jay Leno Show Bombed

In 2009, Jay Leno reluctantly walked away from The Tonight Show. However, he didn't walk far. Leno started hosting The Jay Leno Show on NBC, at 10 p.m. However, the show tanked in the ratings in a big way.

To deflect from that, Leno got the NBC executives to focus on Conan O'Brien's ratings, which were falling. That's all it took for Leno to get his show back.

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

As noted, there's nothing Jay Leno wouldn't do to keep The Tonight Show. He even wore a disguise once! In 2008, Leno was on his way out as host. He decided to wear a disguise, including a bald cap, glasses, and a goatee, to an NBC press conference. Leno asked several questions about himself, including the date of Leno's last show and if he could return as host.

11 Chris Rock Calls Jay Leno A Bad Guy

In 2010, Jay Leno regained his role as host of The Tonight Show. However, several celebs felt Leno had wronged Conan O'Brien. Indeed, most of them took O'Brien's side over Leno. Of course, that made some of his interviews a bit awkward. For example, Chris Rock came out and called Leno a "bad guy." Leno tried to laugh it off, but it created some friction. Rock never appeared as a guest on Leno's show again.

10 Leno Took The Tonight Show Back From Conan O’Brien

In 2004, Jay Leno claimed he wanted to retire in 2010. As mentioned, he'd then hand over the reins to Conan O'Brien. Leno even had a farewell show. However, behind the scenes, Leno felt NBC was forcing him out. By the time 2010 rolled around, Leno had changed his mind. He decided he wanted to keep his show and ended up getting it back in less than a year.

9 He Has Never Admitted To Any Wrongdoing

In 2010, Jay Leno got his show back, and Conan O'Brien was off the air. However, there was a significant fan backlash against Leno. Indeed, most viewers took O'Brien's side in the ordeal.

Leno went on The Oprah Winfrey Show in an attempt to rehab his image. Of course, he refused to accept any responsibility and placed the blame on O'Brien's ratings. He did admit to telling a white lie to O'Brien about handing over the show.

8 Leno Played A Part In Pushing Dennis Miller Out Of Late Night TV

In the 90s, there was a long list of late-night shows. However, rumors suggest Leno and his team did whatever it took to stifle these shows. For instance, Leno's booking team made it almost impossible for Dennis Miller to book guests. It soon got to the point where Miller couldn't compete with the behind-the-scenes tactics. Leno denies there were any booking wars, but Miller claims Leno's lying.

7 Jay Leno And Arsenio Hall Battled In A Late-Night War

In the 90s, Jay Leno took on all late-night hosts, including David Letterman and Dennis Miller. However, his feud with Arsenio Hall was just as ruthless. Leno and Hall went head-to-head in the ratings. Hall said unkind words about Leno and his talent. Also, Hall denies being friends with Leno and doesn't approve of Leno's behavior. Of course, Hall's show went off the air, while Leno's remained a dominant force in TV for years.

6 Jay Leno And Jimmy Kimmel Feud

Jay Leno and Jimmy Kimmel have an unusual "friendship" that goes back a few years. In 2010, Leno threatened to take his show to ABC if NBC wanted to stick with Conan O'Brien. According to Kimmel, Leno befriended him. In the event he moved to ABC, Leno would have knocked Kimmel out of his time slot.

When NBC decided to go with Leno, he never spoke with Kimmel again. Later, Kimmel appeared on The Jay Leno Show and took repeated shots at Leno, to his face.

5 Johnny Carson Refused To Ever Appear On Leno’s Tonight Show

For decades, Johnny Carson was the king of late-night TV. Indeed, Carson made The Tonight Show what it is. However, he didn't approve of Jay Leno as the new host. Instead, he felt David Letterman was the rightful heir to his throne.

As noted, Leno's then-manager planted a fake news story about Carson. The false news story caused bitter feelings on Carson's end, and he refused to ever appear on Leno's Tonight Show. However, he made several appearances on the Late Show with David Letterman on rival network CBS.

4 His Angry Obesity Rant

In April 2019, Jay Leno returned to The Tonight Show for a unique appearance. Of course, new host Jimmy Fallon welcomed Leno back with open arms. Leno finally stepped down as host in 2014, and Fallon took over. However, Leno stirred up some controversy with a rant about obesity. Viewers criticized Leno for his comments and felt they were out of line. Indeed, there are many other things he could talk about instead.

3 Spent Years Making Political Jokes But Feels Comedians Today Should Stay Away From Them

During his tenure as The Tonight Show host, Jay Leno often took aim at political and public figures. In particular, Leno dedicated a lot of his jokes to the Bill Clinton Scandal and the O.J. Simpson trial.

However, in 2019, Leno's feelings on political jokes changed. He now feels that late-night hosts should stay away from politics. Many of his peers pointed out that he spent years focusing on politics.

2 Gabrielle Union Fired From America’s Got Talent After Complaining About Leno’s Comments

As noted, Jay Leno's dubious comments during America's Got Talent stirred up a great deal of controversy. In particular, actress and judge, Gabrielle Union, complained to NBC about the jokes Leno made, which were aimed at Asians. The jokes made Union feel uncomfortable and she felt NBC should edit them out.

However, America's Got Talent added fuel to the fire when producers decided to fire Union for speaking up. Leno said he feels terrible for her and how things worked out.

1 Leno Has Never Apologized To Conan O'Brien

Jay Leno took back over as host of The Tonight Show in 2010. In 2014, he finally handed the show over to Jimmy Fallon. Despite everything that's happened, Leno refuses to apologize. Indeed, he's never apologized to Conan O'Brien and still contends he did nothing wrong. Leno again pushed the idea that O'Brien lost the show simply because of ratings. He refuses to acknowledge his role and still considers himself the good guy in the situation.