Home
Gallery
14 Classic Jay Leno Moments on the 'Tonight Show'

14 Classic Jay Leno Moments on the 'Tonight Show'

Before the host sets up talk-show shop at 10:00 p.m., starting tonight, we look back at 17 years of laughs, stars, surprises, and one very drunk TV cast

By Lynette Rice

Updated September 08, 2009 at 05:00 PM EDT

Skip gallery slides

1 of 14

19. Borat and Martha Stewart — Together Again

Paul Drinkwater/NBCU Photo Bank

Aired: Nov. 9, 2006

Martha Stewart gamely agreed to demonstrate the fine art of bed-making to Sacha Baron Cohen's ever-feisty Borat, who humorously asked where to tie up a woman's arms and legs. Replied a deadpan Stewart: ''On the four posts.'' —Lynette Rice

2 of 14

17. Tribute to Johnny Carson

NBC

Aired: Jan. 24, 2005

The day after Johnny Carson died, guests like Ed McMahon, Bob Newhart, and Don Rickles sat on the couch opposite Leno to pay tribute to the former host of The Tonight Show. —Lynette Rice

3 of 14

15. First-Ever Guest on The Tonight Show With Jay Leno

Chris Haston/NBCU Photo Bank

Aired: May 25, 1992

After performing his first opening monologue (which featured a joke about Vice President Dan Quayle and the controversy over Murphy Brown becoming a single mom), Leno welcomed Billy Crystal as his first guest. Crystal then spoofed Bette Midler's memorable performance of ''You Made Me Love You'' to the retiring Johnny Carson. —Lynette Rice

Continued on next slide.

4 of 14

14. Burying the Hatchet (Temporarily) With Jimmy Kimmel

Paul Drinkwater/NBC

Aired: Jan. 10, 2008

The David Letterman-loving (and formerly Jay Leno-bashing) Jimmy Kimmel let bygones be bygones during the 100-day writers' strike by agreeing to appear on The Tonight Show. The two late-night hosts became kindred spirits during the labor dispute because both were forced to go on the air without the help of their (picketing) comedy scribes. Too bad it didn't last. —Lynette Rice

5 of 14

13. Paul Newman Goes Fast and Furious

Jim Ruymen/Reuters/Corbis

Aired: April 8, 2005

The actor and racing enthusiast takes on Leno in the Indy 500 of go-cart races, handily winning a loop around the soundstages. It's one of the car-crazy host's favorite episodes. —Lynette Rice

6 of 14

11. Katie Couric and Jay Leno Switch Jobs

Paul Drinkwater/NBCU Photo Bank

Aired: May 12, 2003

Leno kicks it with the Today show's Matt Lauer early morning in New York, and Couric stays up way past her bedtime to see how the late-night hosts live. —Lynette Rice

Continued on next slide.

7 of 14

10. The Joke's on Jacko

Margaret Norton/AP Images

Aired: March 4-10, 2005

Leno — forbidden to make fun of Michael Jackson since being called as a witness in his child-molestation trial — invites comedians Roseanne, Dennis Miller, and others to sub in and tell the jokes for him. —Lynette Rice

8 of 14

9. Angie Harmon Says Yes

Paul Drinkwater/NBCU Photo Bank

Aired: March 13, 2000

The Law & Order star thinks she's chatting with Leno to talk up her show until her boyfriend, the New York Giants' Jason Sehorn, surprises her with a marriage proposal. —Lynette Rice

9 of 14

7. Cheers Says Cheers!

Aired: May 20, 1993

Leno takes his show to Boston, where the raucous cast members of Cheers are celebrating the series finale — and most are far too drunk to realize they're actually appearing live. —Lynette Rice

Continued on next slide.

10 of 14

6. Arnold Schwarzenegger Announces Candidacy

Everett Collection

Aired: Aug. 6, 2003

Arnold bypasses the traditional press corps and uses Tonight to announce he'll run for governor of California. Even his advisers, who thought he was staying out of the race, are surprised. —Lynette Rice

11 of 14

4. The Dancing Itos

Neal Preston/Corbis

Aired: March 2, 1995

Leno found endless fodder in the O.J. Simpson trial, eventually turning it into a recurring musical number with a kick line of Judge Lance Itos. —Lynette Rice

12 of 14

3. Bobcat Goldthwait Gets Fired Up

Margaret Norton/NBCU Photo Bank

Aired: May 6, 1994

The antic comedian ignites the guest chair, later claiming that he was avenging the cancellation of The Arsenio Hall Show. —Lynette Rice

Continued on next slide.

13 of 14

2. Barack Obama Interview

Paul Drinkwater/NBC

Aired: March 19, 2009

Obama becomes the first sitting president to appear on a late-night talk show, but causes a small stir when he compares his bowling skills to something out of the Special Olympics. —Lynette Rice

14 of 14

1. Hugh Grant Is Sorry

Margaret Norton/NBCU Photo Bank

Aired: July 10, 1995

After his highly publicized arrest for being caught with a prostitute, the British actor makes his first public appearance on the show, and Leno famously asks, ''What the hell were you thinking?'' The buzzworthy episode cements his ratings hold over David Letterman. —Lynette Rice

Replay gallery

Up Next

By Lynette Rice @LynetteRice

Account

14 Classic Jay Leno Moments on the 'Tonight Show'

1 of 14

19. Borat and Martha Stewart — Together Again

1 of 14

2 of 14

17. Tribute to Johnny Carson

2 of 14

3 of 14

15. First-Ever Guest on The Tonight Show With Jay Leno

3 of 14

4 of 14

14. Burying the Hatchet (Temporarily) With Jimmy Kimmel

4 of 14

5 of 14

13. Paul Newman Goes Fast and Furious

5 of 14

6 of 14

11. Katie Couric and Jay Leno Switch Jobs

6 of 14

7 of 14

10. The Joke's on Jacko

7 of 14

8 of 14

9. Angie Harmon Says Yes

8 of 14

9 of 14

7. Cheers Says Cheers!

9 of 14

10 of 14

6. Arnold Schwarzenegger Announces Candidacy

10 of 14

11 of 14

4. The Dancing Itos

11 of 14

12 of 14

3. Bobcat Goldthwait Gets Fired Up

12 of 14

13 of 14

2. Barack Obama Interview

13 of 14

14 of 14

1. Hugh Grant Is Sorry

14 of 14

Share the Gallery

Up Next

Share the Gallery

Everything in This Slideshow