The BEST episodes of The Tonight Show with Jay Leno season 14

Every episode of The Tonight Show with Jay Leno season 14, ranked from best to worst by thousands of votes from fans of the show. The best episodes of The Tonight Show with Jay Leno season 14!

The Tonight Show with Jay Leno is an American late-night talk show currently hosted by Jay Leno, on NBC. It made its debut on May 25, 1992, following Johnny Carson's retirement as host of The Tonight Show. The nightly broadcast at 23:35 (Eastern) originates from NBC's studios, in Burbank, California.

Last Updated: 12/3/2025Network: NBCStatus: Ended
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#1 - Martha Stewart, Terrence Howard, Big and Rich

Season 14 - Episode 91 - Aired 11/8/2005

Martha Stewart, Terrence Howard, Big and Rich

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#2 - Kurt Russell, Rev. Run, Institute

Season 14 - Episode 81 - Aired 10/18/2005

Kurt Russell, Rev. Run, Institute

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#3 - Dakota Fanning, Charles Barkley, Musashimaru, Christina Aguilera, Herbie Hancock

Season 14 - Episode 82 - Aired 10/19/2005

Dakota Fanning, Charles Barkley, Musashimaru, Christina Aguilera, Herbie Hancock

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#4 - Debra Messing, Ed McMahon, Weezer

Season 14 - Episode 83 - Aired 10/20/2005

Debra Messing, Ed McMahon, Weezer

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#5 - Antonio Banderas, Greg Behrendt, Michael McElroy, Ashlee Simpson

Season 14 - Episode 84 - Aired 10/21/2005

Antonio Banderas, Greg Behrendt, Michael McElroy, Ashlee Simpson

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#6 - Halloween Episode: Rosario Dawson, Ozzy Osbourne

Season 14 - Episode 85 - Aired 10/31/2005

Halloween Episode: Rosario Dawson, Ozzy Osbourne

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#7 - Jimmy Smits, Lisa Marie Presley

Season 14 - Episode 86 - Aired 11/1/2005

Jimmy Smits, Lisa Marie Presley

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#8 - Dr. Phil McGraw, Dennis Rodman, Dwight Yoakam

Season 14 - Episode 87 - Aired 11/2/2005

Dr. Phil McGraw, Dennis Rodman, Dwight Yoakam

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#9 - Nicollette Sheridan, Marc Yu, Fiona Apple

Season 14 - Episode 88 - Aired 11/3/2005

Nicollette Sheridan, Marc Yu, Fiona Apple

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#10 - Jennifer Love Hewitt, John Fogerty

Season 14 - Episode 89 - Aired 11/4/2005

Jennifer Love Hewitt, John Fogerty

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#11 - Dana Carvey, Steve Irwin, Jamiroquai

Season 14 - Episode 90 - Aired 11/7/2005

Dana Carvey, Steve Irwin, Jamiroquai

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#12 - Benjamin Bratt, Robert Downey, Jr., Ryan Cabrera

Season 14 - Episode 80 - Aired 10/17/2005

Benjamin Bratt, Robert Downey, Jr., Ryan Cabrera

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#13 - Nicole Richie, Jon Favreau

Season 14 - Episode 92 - Aired 11/9/2005

Nicole Richie, Jon Favreau

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#14 - Garth Brooks, Patricia Arquette

Season 14 - Episode 93 - Aired 11/10/2005

Garth Brooks, Patricia Arquette

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#15 - Eva Longoria, Collin Kelly, Kenny Chesney

Season 14 - Episode 94 - Aired 11/11/2005

Eva Longoria, Collin Kelly, Kenny Chesney

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#16 - Jason Lee, Usher, Neil Diamond, Brian Wilson

Season 14 - Episode 95 - Aired 11/14/2005

Jason Lee, Usher, Neil Diamond, Brian Wilson

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#17 - Melissa Etheridge

Season 14 - Episode 96 - Aired 11/15/2005

Melissa Etheridge

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#18 - Hugh Laurie, Joan Embery, George Clinton

Season 14 - Episode 97 - Aired 11/16/2005

Hugh Laurie, Joan Embery, George Clinton

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#19 - Jerry Seinfeld, Shelley Berman, Carrie Underwood

Season 14 - Episode 98 - Aired 11/17/2005

Jerry Seinfeld, Shelley Berman, Carrie Underwood

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#20 - Teri Hatcher, Cedric the Entertainer, Sheryl Crow

Season 14 - Episode 99 - Aired 11/18/2005

Teri Hatcher, Cedric the Entertainer, Sheryl Crow

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#21 - Jimmy Carter, Wentworth Miller, Eurythmics

Season 14 - Episode 100 - Aired 11/21/2005

Jimmy Carter, Wentworth Miller, Eurythmics

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#22 - Denise Richards, Liz Phair, Emeril Lagasse

Season 14 - Episode 70 - Aired 10/3/2005

Denise Richards, Liz Phair, Emeril Lagasse

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#23 - Lindsay Lohan, John Krasinski, Sergio Mendes, The Black Eyed Peas

Season 14 - Episode 209 - Aired 5/9/2006

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#24 - Paul Bettany, Duff Goldman, Nick Lachey

Season 14 - Episode 210 - Aired 5/10/2006

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#25 - Tom Cruise, Michelle Rodriguez

Season 14 - Episode 211 - Aired 5/11/2006