9 of Jay Leno's Greatest Hits From His ‘Tonight Show’ Run

9 of Jay Leno's Greatest Hits From His 'Tonight Show' Run

From the Dancing Itos to Jaywalking, a look at Leno's top moments on NBC

“Tonight Show” host Jay Leno will say his last goodbye on Thursday night, his last show before handing over the reins to Jimmy Fallon.

From his infamous interview with a contrite Hugh Grant to the Dancing Itos and Jaywalking, here are some of Leno's best moments from the “Tonight Show” and the short-lived “Jay Leno Show” on NBC.

Also read: From Steve Allen to Jay Leno – All of ‘Tonight Show's’ Hosts and Sidekicks Before Jimmy Fallon (Photos)

Hugh Grant – 1995
The British actor known for playing stammering characters had recently been caught cheating on his longtime girlfriend, actress Elizabeth Hurley, with a prostitute. And Leno — not David Letterman or Oprah or even Ted Koppel — asked Grant the question on everyone's minds: “What the hell were you thinking?”

The O.J. Trial & Dancing Itos – 1995
Leno got a ton of mileage out of the “Trial Out of the Century.” The Dancing Itos — five dancing versions of the judge presiding over O.J. Simpson's trial, Lance Ito — made their debut in March 1995.

Also read: Jay Leno on ‘Tonight Show’ Ouster: ‘I Was Blindsided'; Compares Jimmy Fallon to Johnny Carson (Video)

Go-Karting with Paul Newman – 2005
Oscar winner and food impresario Paul Newman visited the “Tonight Show” in 2005 to talk cars with auto enthusiast Leno. Of course, the host couldn't pass up the opportunity to challenge Newman — a long-time racing buff — to a go-kart race around the studio.

President Obama – 2009
Leno landed the first ever interview with a sitting president on a late-night talk show when President Obama visited in March 2009, just a few weeks into Obama's first term. Obama has been on the “Tonight Show” twice since, as well as “Late Night With Jimmy Fallon” and rival “Late Show With David Letterman” on CBS.

Also read: Jay Leno on ‘Tonight Show’ Exit: 5 Other Surprising Quotes From His '60 Minutes’ Interview (Video)

Best of Jaywalking – 2009
Back in May 2009, when Leno had his first “Tonight Show” final bow, the host put together a highlight reel with some of his favorite interviewees on “Jaywalking,” the timeless segment that highlights the basic street knowledge of your neighbors and mine.

Best of Headlines
By the same token, Leno's weekly “Headlines” segment was always a fan favorite.

Also read: Jay Leno, Julia Louis-Dreyfus Among Television Academy's Hall of Fame Inductees

Kanye's Apology – 2009
Not all of Leno's greatest moments during his nonconsecutive 22-year span as “Tonight Show” host occurred when he was actually the “Tonight Show” host. Who can forget those awkward few months when he had his own 10 p.m. “Jay Leno Show”? Though that series was a flop, it yielded a few nuggets, like this impromptu apology from rapper Kanye West for interrupting Taylor Swift at MTV's Video Music Awards.

Jimmy Kimmel – 2010
When Leno returned to the “Tonight Show,” he brought rival late show host Jimmy Kimmel on for a 10-questions segment. Little did Leno know the ABC host would take the opportunity to ridicule him over the whole debacle.

Also read: Jay Leno Mocks Dems More Than GOP, New Study Finds

NBC Battles — 2013
By the end of his run on the “Jay Leno Show,” the host was barely concealing his contempt for the NBC's blunderous decision-making. When rumors that NBC was planning to replace him with Jimmy Fallon at the helm of the “Tonight Show” started circulating in 2013, Leno started throwing regular barbs at network brass, including calling NBC execs “snakes” in one joke.

But, as we now know, Leno has graciously passed the torch to Fallon, who takes the chair when the “Tonight Show” returns on Feb. 17.

  • Sean Murdock

    Couldn't even come up with a full “Top Ten” … says it all, really.

    • Damien W

      Beat me to it!

  • EllenFD

    Jay Leno was a very watchable host and expert monologist. He put up with a lot of undeserved rancor with gracious good humor. I wish him well.

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  • Uh hum

    With Fallon, NBC is turning the late night format into improv humor for comic speed freaks when it was really meant for mature folks looking to wind down before bedtime. The ageist makeover will bomb and NBC will continue its fall as a 3rd rate network.

  • LST

    Truly sickening to see him go, no one can ever top Jay Leno, especially Fallon who is about as funny as a train wreck/plane crash combo. NBC; Nothing But Crap.

    • Gardener

      Totally concur. Leno was a professional and true gentlemen. You only to witness the respect poured out to him during the last shows.

  • cmen

    Leno was king and Letterman should be put out to pasture, he still thinks funny is lifting his socks and making noises. Fallons a kids show and will die off, Kimble can be an ass but he should go to CBS and get rid of Letterman. Jay and his writers always have the best jokes, Carson was the best but Jay was a close second and should have had 5 more years…………

  • Calvin Gregory

    I used to think Jay was funny, but then he got into that comfortable un-edgy sort of groove, which made him more palatable to the older crowd (not old just older). Letterman got soft as he aged but still could be funny when he wasn't being to acidic and political. I never found Fallon funny on SNL and I still do not see what the attraction to him is, the Tonight Show tradition of quality ends with Jay (even though I have issues with him, he's better than fallon by a long shot). Conan is funny and I know this thread isn't the best place to say that, but he's in a different space now. Really, I think the only one who still makes me really laugh is Craig Ferguson. But, he's happy where he is. If Dave should retire soon he should give it to Conan. As he did with his old show. Fallon is a huge mistake. I guess people who liked Napoleon Dynamite might find it funny. Seems most things that are considered popular with the youth are movies that aren't funny by any real measure of comedy. Remember Dangerfield? remember Pryor? or Tim Allen at his best. There are no true jokes anymore just insipid inane sound bites. Just because you are silly and animated doesn't mean you are good with physical humor, it means you have nothing left to offer us.

  • brightstar

    Jay Leno is the BEST! So sad to see him go. He was the best host of the Tonight Show & is the best comedian around, IMO. Others come close, but who could keep up the pace for 22 years like he did — Number 1 !!!

    My heart still hurts about the way he has been treated. I don't know why I'm taking it so personally, except fellow feeling perhaps. All the disrespect, the mean comments — all so unnecessary. Everyone who has said horrible things about him are little people who will never match his professionalism, his kindness, his graciousness. They look bad and he continues to look like the good guy, which he is, I think. Nobody says anything about all his good works, the nice things he has done for people, probably because he doesn't flaunt it, but this is a really great human being, a very hard worker, and deserves our respect and love, not what he's been getting. Except his job at The Tonight Show, of course. He should still be there.

    • CubFanJohn

      Leno was good but nobody will ever replace Johnny Carson!!

  • Jeni Leeth

    My favorite show was the lady who gave mouth to mouth to aher rooster and Terry Bradshaw and Jay Leno with all thier wise cracks. That is the show I would like to have a video of. Hillarious. You will be greatly missed Jay Leno.

  • pd

    I'm now part of the old crow (60) and love Fallon… just wish he'd leave the politics out of his act…

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