The BEST episodes of The Tonight Show with Jay Leno season 16

Every episode of The Tonight Show with Jay Leno season 16, 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 16!

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: 5/16/2024Network: NBCStatus: Ended
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#1 - Anne Hathaway; Gabriel Iglesias; Amos Lee

Season 16 - Episode 139 - Aired 6/16/2008

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#2 - Don Rickles, Josh Flitter, Dashboard Confessional

Season 16 - Episode 4 - Aired 6/7/2007

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#3 - Bernie Mac, Cat Deeley, Chris Cornell

Season 16 - Episode 3 - Aired 6/6/2007

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#4 - George Clooney, Rihanna

Season 16 - Episode 2 - Aired 6/5/2007

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#5 - John Larroquette, Chelsea Handler, Matchbox Twenty

Season 16 - Episode 73 - Aired 10/4/2007

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#6 - Tom Selleck, Carlos Mencia, Bobbie and Willie Nelson, Ed Asner

Season 16 - Episode 72 - Aired 10/3/2007

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#7 - Bill Cosby, Landon Pigg

Season 16 - Episode 99 - Aired 3/12/2008

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#8 - America Ferrara, Bob Saget, The Blind Boys of Alabama

Season 16 - Episode 98 - Aired 3/11/2008

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#9 - Dominic Monaghan, Ethan Bortnick, Sheryl Crow

Season 16 - Episode 97 - Aired 3/10/2008

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#10 - Gordon Ramsay

Season 16 - Episode 78 - Aired 10/11/2007

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#11 - Brad Garret; Ingrid Michaelson; John Melendez

Season 16 - Episode 100 - Aired 4/15/2008

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#12 - Ellen Degeneres; Jerry O'Connell; Jazmine Sullivan

Season 16 - Episode 194 - Aired 9/30/2008

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#13 - Steve Carell, Kenny Smith, Goo Goo Dolls

Season 16 - Episode 5 - Aired 6/8/2007

Ryan Phillippe; Lisa Lampanelli; Jim Lauderdale
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#14 - Ryan Phillippe; Lisa Lampanelli; Jim Lauderdale

Season 16 - Episode 140 - Aired 3/19/2008

Ryan Phillippe from "Stop-Loss", Lisa Lampanelli from "Drillbit Taylor" and music of Jim Lauderdale from the CD "Honey Songs".

Dave Salmoni; Patricia Arquette; Punch Brothers
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#15 - Dave Salmoni; Patricia Arquette; Punch Brothers

Season 16 - Episode 132 - Aired 2/29/2008

Amazing animals with Dave salmoni! From "medium" Patricia Arquette! The music of Punch Brothers! " Jaywalking."

Dana Carvey; Malin Akerman; Plain White T's
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#16 - Dana Carvey; Malin Akerman; Plain White T's

Season 16 - Episode 77 - Aired 10/10/2007

Dana Carvey; Malin Akerman ("The Heartbreak Kid"); Plain White T performs from the CD "Every Second Counts."

Jamie Pressly; Brady Barr; Blue Man Group
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#17 - Jamie Pressly; Brady Barr; Blue Man Group

Season 16 - Episode 76 - Aired 10/9/2007

Jamie Pressly ("My Name is Earl"); National Geographic's Brady Barr; Blue Man Group performs.

Cate Blanchett; Tyler Perry; Annie Lennox
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#18 - Cate Blanchett; Tyler Perry; Annie Lennox

Season 16 - Episode 74 - Aired 10/5/2007

Cate Blanchett ("Elizabeth: The Golden Age"); Tyler Perry ("Why did I get Married"); Annie Lennox performans from the CD "Songs of Mass Destruction."

Jason Lee; Pat Monahan
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#19 - Jason Lee; Pat Monahan

Season 16 - Episode 71 - Aired 10/2/2007

Jason Lee ("My Name is Earl"); Kristin Chenoweth ("Pushing Daisies"); Pat Monahan performs from the CD "Last of Seven."

Conan O'Brien; Anderson Cooper; Allison Moorer
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#20 - Conan O'Brien; Anderson Cooper; Allison Moorer

Season 16 - Episode 147 - Aired 3/27/2008

Conan O'Brien; Anderson Cooper; Allison Moorer: Performance from the CD "Mockingbird"; and Mo Rocca on spring break in Florida.

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#21 - Terry Bradshaw; Ray Sanders; Colbie Caillat

Season 16 - Episode 188 - Aired 5/23/2008

Terry Bradshaw; Turkey baster virtuoso Ray Sanders; Colbie Caillat: Performance from the CD "Little Things;" Amaon.com's Worst Sellers.

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#22 - Laura & Jenna Bush; David Cook; Tristan Prettyman

Season 16 - Episode 187 - Aired 5/22/2008

Laura & Jenna Bush; American Idol winner David Cook; Tristan Prettyman: Performance from the CD "Hello"; Brian Herzlinger Talks to Third Graders who Want to become a President.

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#23 - Adam Sandler; Hillary Duff; Al Green

Season 16 - Episode 186 - Aired 5/21/2008

Adam Sandler "You Don't Mess with the Zohan"; Hillary Duff "War, Inc."; Al Green: Performance from the CD "Lay It Down"; Summer Movie Knockoffs.

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#24 - John and Elizabeth Edwards, Maz Jabroni

Season 16 - Episode 16 - Aired 6/25/2007

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#25 - Bill Maher, Minnie Driver

Season 16 - Episode 26 - Aired 7/16/2007