The WORST episodes of Late Show with David Letterman

Every episode of Late Show with David Letterman ever, ranked from worst to best by thousands of votes from fans of the show. The worst episodes of Late Show with David Letterman!

An hour-long weeknight comedy and talk show broadcast by CBS from the Ed Sullivan Theater on Broadway in New York City and is produced and hosted by David Letterman. The show's music director and bandleader of the house band, the CBS Orchestra, is Paul Shaffer. The head writers are brothers Justin Stangel and Eric Stangel. The announcer is Alan Kalter, who replaced Bill Wendell as announcer in 1995. The show airs at night, but is recorded the afternoon of the broadcast.

Last Updated: 12/11/2025Network: CBSStatus: Ended
Reese Witherspoon, Harry Connick Jr.
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#1 - Reese Witherspoon, Harry Connick Jr.

Season 16 - Episode 50 - Aired 11/25/2008

Dave calls out Tony for making him read the same monologue joke twice; after President Bush pardoned 14 convicted felons that week, Dave and Alan grant clemency to an audience member; Reese Witherspoon relives her 2005 Oscar win and plugs Four Christmases; Harry Connick Jr. performs "It's The Most Wonderful Time of the Year."

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#2 - Alec Baldwin, Paul Mooney, Ryan Adams

Season 16 - Episode 32 - Aired 10/29/2008

Alec Baldwin, Paul Mooney, and Ryan Adams & The Cardinals are the scheduled guests.

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#3 - Regis Philbin, James Taylor

Season 16 - Episode 31 - Aired 10/28/2008

Regis Philbin and James Taylor are the scheduled guests.

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#4 - Bill O'Reilly, Lauren Conrad

Season 16 - Episode 30 - Aired 10/27/2008

Bill O'Reilly and Lauren Conrad are the scheduled guests.

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#5 - Katie Couric, Dev Patel, Mr. Brownstone

Season 16 - Episode 46 - Aired 11/19/2008

Day 3 of "Tribute Band Week" with Mr. Brownstone. Plus, Katie Couric!

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#6 - Carla Bruni Sarkozy, Jack Hanna, Cold Hard Cash

Season 16 - Episode 45 - Aired 11/18/2008

With First Lady of France Carla Bruni Sarkozy on the show, Dave wonders if he'll accidentally start an international incident; Lyle the Intern and his pal "Rudy" (Joe Grossman) promote their internet show; Jack Hanna brings out a baby kangaroo, an aardvark, and a macaque; on Day 2 of Tribute Band Week, The Cold Hard Cash Show performed "Folsom Prison Blues."

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#7 - Emma Thompson, Michelle Felicetta, Purple Reign

Season 16 - Episode 44 - Aired 11/17/2008

Emma Thompson and fox attack survivor Michelle Felicetta are the scheduled guests. Plus, Day 1 of "Tribute Band Week" with Purple Reign!

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#8 - Bill Cosby, Matt Braunger

Season 16 - Episode 43 - Aired 11/14/2008

A plug for Tribute Bands Week; Bill Cosby does some stand-up, promotes the "Cosby Show" complete series DVD set and comments on the election; The Answer (making their American TV debut) performed "Never Too Late."

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#9 - Brian Williams, Tim Robbins

Season 16 - Episode 19 - Aired 10/3/2008

Dave comments on the previous night's vice-presidential debate, which is followed by a string of Unfair Edits; NBC anchorman Brian Williams also throws in his two cents; Tim Robbins talks baseball, shares a story about Paul Newman, and plugs City of Ember.

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#10 - Ashley Olsen, Paul Rudd, John Legend

Season 16 - Episode 33 - Aired 10/30/2008

"New Halloween Costumes" include Sarah Palin's passport, the Dow Jones Industrial Average, Amy Winehouse's hair, and an oversized copy of the Fun Facts book; Cole Hamels of the World Champion Philadelphia Phillies reads the Top Ten; John Legend performed "I Love, You Love."

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#11 - Nicole Kidman, Simon Baker, Kanye West

Season 16 - Episode 49 - Aired 11/24/2008

Nicole Kidman, Simon Baker, and Kanye West are the scheduled guests.

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#12 - James Franco, Bruce McCall, The Allstarz

Season 16 - Episode 48 - Aired 11/21/2008

James Franco and Bruce McCall are the scheduled guests. Plus, Day 5 of "Tribute Band Week" with The Allstarz!

Stephen Colbert, Kristen Stewart, Super Diamond
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#13 - Stephen Colbert, Kristen Stewart, Super Diamond

Season 16 - Episode 47 - Aired 11/20/2008

Stephen Colbert and Kristen Stewart are the scheduled guests.

Bruce Willis, Sia
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#14 - Bruce Willis, Sia

Season 16 - Episode 42 - Aired 11/13/2008

Bruce Willis and Sia are the scheduled guests.

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#15 - Show #2777

Season 14 - Episode 131 - Aired 4/24/2007

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#16 - Show #2776

Season 14 - Episode 130 - Aired 4/23/2007

Top Ten list presented by Sanjaya Malakar

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#17 - Show #2775

Season 14 - Episode 129 - Aired 4/20/2007

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#18 - Show #2770

Season 14 - Episode 124 - Aired 4/13/2007

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#19 - Marcia Cross, Alan Zweibel

Season 16 - Episode 34 - Aired 10/31/2008

Marcia Cross, Alan Zweibel, and George Clinton are the scheduled guests.

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#20 - Paris Hilton, Elvis Costello, Jenny Lewis, a Top Ten List by Ricky Gervais

Season 16 - Episode 35 - Aired 11/3/2008

Paris Hilton, Elvis Costello, and Jenny Lewis are the scheduled guests. Plus, a Top Ten from Ricky Gervais!

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#21 - Tom Brokaw, Vera Farmiga

Season 16 - Episode 36 - Aired 11/5/2008

Dave shares a few thoughts on election night; an audience member panics when he realizes he forgot to vote; Tom Brokaw promotes his best-selling book, "Boom!"; a very pregnant Vera Farmiga plugs The Boy in the Striped Pajamas.

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#22 - Ben Stiller, Q-Tip

Season 16 - Episode 37 - Aired 11/6/2008

Ben Stiller and Q-Tip the scheduled guests. Plus, the Kid Scientists of Naperville, IL!

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#23 - Natalie Portman, Artie Lange, Brad Paisley

Season 16 - Episode 38 - Aired 11/7/2008

Alec Baldwin endorses the Fun Facts book; Natalie Portman discusses campaigning for President-elect Obama; Bill Scheft begs the new president to make an ass of himself; Artie Lange plugs his new book; Brad Paisley performed a cover of The Cars' "Good Times Roll."

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#24 - Ted Turner, Jamie Oliver, Taylor Swift

Season 16 - Episode 39 - Aired 11/10/2008

Ted Turner, Jamie Oliver, and Taylor Swift are the scheduled guests.

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#25 - Don Rickles, Amy Brenneman, Alicia Keys

Season 16 - Episode 40 - Aired 11/11/2008

Dave shows a clip of King Tut's mummy appearing on Maury; NFL superstar Terrell Owens presents the Top Ten; the legendary Don Rickles plugs his new book and riffs on marriage and growing old; Alicia Keys performed "The Thing About Love."