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: 11/19/2024Network: CBSStatus: Ended
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#1 - 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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#2 - Russell Brand, Charlie Haden

Season 16 - Episode 41 - Aired 11/12/2008

Russell Brand and Charlie Haden are the scheduled guests. Plus, Stupid Human Tricks!

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#3 - 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."

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#4 - 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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#5 - 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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#6 - 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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#7 - 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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#8 - 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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#9 - 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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#10 - Teri Hatcher, Ludacris

Season 16 - Episode 51 - Aired 11/26/2008

Teri Hatcher, Ludacris, and T-Pain are the scheduled guests.

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#11 - 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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#12 - 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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#13 - 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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#14 - 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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#15 - 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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#16 - 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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#17 - 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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#18 - 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.

Denis Leary, John Mayer
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#19 - Denis Leary, John Mayer

Season 16 - Episode 52 - Aired 11/27/2008

Denis Leary and John Mayer are the scheduled guests. Plus, Dave's Mom and the 16th annual pie-guessing contest!

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#20 - Tom Arnold, Faith Hill

Season 16 - Episode 53 - Aired 11/28/2008

Bruce Willis promotes the Fun Facts book, declaring the tome "Yippee-ki-larious, mother****er!"; Tom Arnold laments the failure of his third marriage and plugs Gardens of the Night; Dave chats with a grouchy CBS Store employee (Johnny Dark); Faith Hill and the Morgan State University Choir performed "Little Drummer Boy."

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#21 - Jennifer Connelly, Anderson Cooper, The Duke Spirit

Season 16 - Episode 54 - Aired 12/8/2008

Jennifer Connelly, Anderson Cooper, and The Duke Spirit are the scheduled guests. Plus, a special Top Ten from the Ball State University football team!

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#22 - Amy Adams, Michael Sheen, Jamey Johnson

Season 16 - Episode 55 - Aired 12/9/2008

Amy Adams, Michael Sheen, and Jamey Johnson are the scheduled guests.

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#23 - Keanu Reeves, Paula Abdul, Loudon Wainwright III

Season 16 - Episode 56 - Aired 12/10/2008

Keanu Reeves, Paula Abdul, and Loudon Wainwright III are the scheduled guests.

Sen. John McCain, Bon Iver
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#24 - Sen. John McCain, Bon Iver

Season 16 - Episode 57 - Aired 12/11/2008

Sen. John McCain and Bon Iver are the scheduled guests.

Meryl Streep, Jeff Altman
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#25 - Meryl Streep, Jeff Altman

Season 16 - Episode 58 - Aired 12/12/2008

In need of a pick-me-up, Dave repeats the sneezing monkey clip; a bronchitis-stricken Meryl Streep promotes Doubt; Dave's old buddy Jeff Altman does a few impressions.