Jay Leno’s Late-Night Legacy

by | May 28, 2009 at 5:00 PM | Cover Story, TV News

After nearly 20 years on late night and one year shy of his 60th birthday, Jay Leno is finally ready to be a primetime player.

But before Leno makes his landmark move to 10 p.m. this fall, he must say goodbye to ‘The Tonight Show,’ and at least he can walk off that stage with a grin–and that chin–knowing he went out on top.

See Billy Crystal’s surprise goodbye to Jay.

What would a proper send-off be without a Top list? We’ve pulled together our favorite moments from the last 17 years of ‘The Tonight Show with Jay Leno.’

Jay Leno’s 15 Greatest Moments on ‘The Tonight Show’

15. It’s a…’she’! (Sept. 27, 2005)
Let’s face it, Jay Leno isn’t exactly known for his interviewing skills–he’s a jokes man–but Jay spawned a baby-bump-obsessed tabloid tizzy when Jennifer Garner’s pronoun slip revealed the sex of her first child with Ben Affleck. WHOOPS!

14. Martha + Borat + A Bed = Brilliant (Nov. 9, 2007)
Martha Stewart has done hard time and that’s no joke, but who knew the Domestic Goddess would emerge the comedic genius in a bit where she teaches Borat (Sacha Baron Cohen) the “proper” way to make a bed?

Watch Jay’s take on only one more day.

13. Daredevil Avoids Disaster (Sept. 20, 1996)
“Kaptain” Robbie Knievel–daredevil Evel Knievel’s son–made a “death-defying” 150-foot motorcycle jump during the show in an over-hyped–and ultimately anticlimactic–stunt. Maybe Fonzie jumping the shark would have been better?

12. ‘Medium’ Kid Disses Clooney! (Jan. 2, 2007)
Scene-stealing 10-year-old Maria Lark of ‘Medium‘ served Hollywood heartthrob George Clooney a slice of humble pie when she revealed–as he sat next to her–that she thinks ‘Pirates of the Caribbean‘ hunk Orlando Bloom is way better then him. Good sport Clooney, naturally, laughed.

Watch ‘Tonight Show’ Clips Here

11. Trading Places (May 12, 2003)
We’re not ones to fall for a sweeps-tastic ratings stunt, but we have to admit it was fun to watch then ‘Today Show‘ host Katie Couric stay up late and Jay Leno get up early when the hosts swapped jobs for a day.

10. Heidi Klum Goes Bust (Oct. 14, 2003)
Supermodel Heidi Klum breathes…and breaks her $11-million dollar Victoria Secret bra, while trying to yodel. Well, she is German. And named Heidi.

9. The Amazing Race (April 8, 2005)
Car enthusiast Jay Leno and racing enthusiast Paul Newman had a go-cart race around the NBC Studios, and even at age 80, the Hollywood legend whooped the talk show host’s butt. (Who cares if he let him win?)

8. What in the Blazes? (May 6, 1994)
Forgotten comic Bobcat Goldthwait claims an unforgettable moment on the list when he lit the guest chair on fire in protest of…something we forget. (The jokester was fined for the prank.) Now if we could just forget about his unintelligible screeching too.

7. The Proposal (March 13, 2000)
Nevermind the stadium Jumbotron. NFL star Jason Sehorn chose to nationally broadcast those four magic words–’Will you marry me?‘–to a jaw-droppingly stunned Angie Harmon (‘Law & Order‘) during her appearance on the show. Three daughters and a decade later, the couple is still together. Leno should play Cupid more often!

6. Dancing with the Trial Stars (March 2, 1994)
The O.J. Simpson murder trial became a national obsession and Leno capitalized on that by spoofing Judge Lance Ito in a musical number that became one of the show’s most popular sketches. Who could forget the ‘The Dancing Itos?’ Especially when they’re dressed like The Village People!

Take a look at Leno’s famous guests in our photo gallery.

5. Muzzle? Tough! (March 4, 2005)
Gag order be damned! The Wacko Jacko jokes will go on! When Leno was named a witness in the Michael Jackson trial, he was ordered not to discuss it on the show. Leno’s clever way around it? Bringing in stand-in stand-ups Dennis Miller, Brad Garrett, and Roseanne Barr to tell the jokes for him.

4. The Announcement (Aug. 6, 2003)
The moment ‘The Terminator’ became ‘The Governator’ surprised everyone. Arnold Schwarzenegger stayed ‘Hollywood’ when he chose to announce his run for governor of California…on ‘The Tonight Show.’

3. A Notch in History (March 19, 2009)
President Barack Obama became the first sitting President to appear on a late-night talk show when he appeared on Leno’s show for the second time. (Too bad Obama’s ‘Special Olympics’ faux pas got the bulk of the attention.)

2. Cheers to That! (May 20, 1993)
When the classic sitcom ‘Cheers‘ went off the air after its 11-year run, the cast went out in style. Oh wait. No they didn’t. They went out completely bombed! The stars appeared on ‘The Tonight Show’ for a live series finale celebration, and they all turned up drunk. It was ‘Must-See’ TV, indeed. But what did you expect from a show about a beloved bar?

1. ‘What the hell were you thinking?!’ (July 10, 1995)
Hugh Grant. Divine Brown. Sunset Boulevard. $50. And Elizabeth Hurley at home. Seriously, what was he thinking? The ‘Love Actually‘ star’s notorious arrest–and infamous ‘Tonight Show’ apology–helped the humiliated actor successfully avert career disaster (he is, however, still single). Now that’s a hell of a trick.

And with that, Jay Leno says good night to late night on Friday, May 29th. He joins the exclusive club of former hosts–Steve Allen (1954-1957), Jack Paar (1957-1962), and Johnny Carson (1962-1992)–and passes the torch to fellow NBC comedian Conan O’Brien, who also happens to be Leno’s final guest.

Click here to see which celebrities are helping Conan adjust to the throne when he begins his reign as ‘Tonight Show’ host starting June 1st.

What are your favorite Leno moments?