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Season guide

Late Show with David Letterman: Season 14

199 episodes Premiered Aug 28, 2006 Updated Sep 25, 2026
Previously on Late Show with David Letterman

Season 14 Lore Primer

Key plot threads, lore context, and character stakes you need to remember before diving into this season.

  • ⚡ Directly follows the overarching narrative developments of Late Show with David Letterman Season 13.
  • ⚡ Faction dynamics and core character alliances shift under escalating external stakes.
  • ⚡ Crucial mysteries introduced previously reach key turning points and narrative reckonings.
  • ⚡ Sets up serialized story arcs that build directly toward the climactic season finale.
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Season 14 Episodes

Episode Guide

🛡️ SPOILER SHIELD

Season 14 Progress Shield

Future titles & synopses blurred. Tap "Reveal" on any card to peek.
Binge Efficiency Engine

Season 14: Filler vs. Essential Canon

Filter episodes by narrative weight. Focus on essential mytharc and skip standalone side quests.

97%
Mytharc (5): Crucial lore & season climaxes
Core (194): Character development & subplots
Side Quest (0): Standalone / filler
S14·E2 Core

Zach Braff, Jeff Brendenburg, The Roots

Aug 29, 2006

Dave toys around with the new product from Apple Computers, the "I-Stinguisher"; a man in pajamas and a bathrobe asks Dave where he would find some coffee; writer Jeff Bredenberg p

S14·E3 Core

Snoop Dogg, Charlie Hill, OK Go

Aug 30, 2006

In honor of the show's 13th anniversary, an intern accidentally walks onstage to ask Dave to sign his own greeting card; live from Tracy, California, Ron Patrick drives around in a

S14·E4 Core

Julianne Moore, radio-show hosts Opie and Anthony

Aug 31, 2006

Tony visits The Hamptons, where he complains about traffic; recently embarassed CNN anchor Kyra Phillips presents the Top Ten; 5,000 tennis balls are dropped onstage; Opie & Anthon

S14·E10 Core

Johnny Knoxville, Rachael Ray

Sep 15, 2006

Johnny Dark measures Dave's inseam, much to his chagrin; while promoting "Ventriloquist Week" for the umpteenth time, Dave argues with his very own dummy; to mark the end of summer

S14·E12 Core

Patrick Dempsey, Jay Johnson and Darwin, Kasabian

Sep 19, 2006

Ventriloquist Week, Day 2: Jay Johnson jokes about evolution while his primate friend Darwin sings "Send in the Clowns" in his "native" tongue; a safe is thrown out an 8th floor wi

S14·E15 Core

LeBron James, Todd Oliver and Irving, Ludacris

Sep 22, 2006

Ventriloquist Week, Day 5: Todd Oliver has a conversation with his talking dog, Irving; Dave and Lebron James shoot baskets on 53rd Street; Ludacris performed "Money Maker."

S14·E17 Core

Billy Bob Thornton, Lily Capehart, Sean Lennon

Sep 26, 2006

Ten-year-old "lizard charmer" Lily Capehart puts her amphibian pets in doll costumes; Billy Bob Thornton promotes "The School for Scoundrels"; Sean Lennon performed "Wait For Me."

S14·E35 Core

Bill O'Reilly, Jeff Altman, Tilly and the Wall

Oct 27, 2006

Dave shows off new photos of Harry; Dave Dorsett leaves his station to goof around with a sock puppet; Dave and Bill O'Reilly have another heated discussion about current events; T

S14·E38 Core

Gary Sinise, Joanne Carson, Jim Norton

Nov 1, 2006

Dave plugs the upcoming Ball State-Michigan football game and promises to give a nickel to everyone that attends the game; Dave reads a letter from a fan pertaining to staff hostil

S14·E40 Core

Martin Short, Kinky Friedman

Nov 3, 2006

Martin Short performs a song-and-dance number about the internet's role in his sexless marriage; country singer/novelist/gubernatorial candidate Kinky Friedman lays down his agenda

S14·E41 Core

Will Ferrell, Jack Hanna

Nov 6, 2006

Britney Spears drops by looking for Will Ferrell; at the end of his interview, Will ad-libs through a selection from "Phantom of the Opera"; Jack Hanna introduces Dave to Fluffy th

S14·E42 Core

Dustin Hoffman, Jamie Oliver, The Metropolitan Opera

Nov 8, 2006

Outgoing Defense Secretary "Donald Rumsfeld" (Gerard) fields questions from the audience; Jamie Oliver makes sausage carbonara; the Metropolitan Opera performs a selection from the

S14·E43 Core

Kiefer Sutherland, Jenna Fischer, Rocco DeLuca

Nov 9, 2006

Live via satellite, Biff walks through a six-acre corn maze in Livermore, California. By the end of the show, Dave asks him if he's scared, prompting Biff to snap back, "It takes a

S14·E46 Mytharc

Jack Black & Kyle Gass, Fred Travalena, Tenacious D

Nov 14, 2006

Impressionist Week, Day 2: Frank Travalena closes his set by mimicing every president from Kennedy to Dubya. Also, Tenacious D (Jack Black and Kyle Gass) promote their new movie an

S14·E50 Core

Jerry Seinfeld, Dan Patrick

Nov 20, 2006

Tonights guests include Jerry Seinfeld and Dan Patrick. Plus, a public apology from Jerry's former co-star Michael Richards.

S14·E51 Core

Hugh Jackman, Chris Elliott, Jimmie Johnson

Nov 21, 2006

Tonight's "Rejected FDA Products" include Hebrew National Bacon, Frozen Mayonnaise Bars (which Dave tastes), and OJ Simpson's "I Can't Believe It's Not Butter, But If I Did Believe

S14·E53 Core

Eugene Levy, John Mayer

Nov 23, 2006

Dave shows footage of the staff Thanksgiving dinner, which includes a drunk Biff telling off Dave and a turkey carver severing his hand; Dave correctly guesses that his mother made

S14·E57 Core

Richard Simmons, Kate Walsh, Ciara

Nov 29, 2006

A giant goat knocks over the Rockefeller Center Christmas Tree; Andy Kindler visits the US Marshals Training Academy in Georgia; in his first Late Show appearance in six years, Ric

S14·E61 Core

Howard Stern, Gwen Stefani

Dec 12, 2006

Tonight at Hello Deli, Dave and Rupert dare a (alleged) SUNY student from Queens to eat a Taco Bell chalupa; Howard Stern walks onstage in a Father Christmas outfit, giving out fre

S14·E63 Core

Will Smith, Evanescence

Dec 14, 2006

An irate staffer gives Dave a holiday-themed "f*** you"; "Senator Hillary Rodham Clinton" (Gerard) fields questions from the audience; Will Smith promotes The Pursuit of Happyness

S14·E64 Core

Clint Eastwood, Matthew Fox

Dec 15, 2006

Tonight's guests include Clint Eastwood and Matthew Fox are the scheduled guests.

S14·E75 Core

Penelope Cruz, Gary Mule Deer, Ben E. King

Jan 9, 2007

A woman from Chicago plays "Name That Smell" at Hello Deli; after vilifying Commonwealth Edison, Alan gets beaten up by one of their employees; Ben E. King performs "Stand By Me."

S14·E76 Core

Peter O'Toole, Marc Maron

Jan 10, 2007

Tonight's guests are Peter O'Toole and Marc Maron, plus a Top Ten from baseball legends Cal Ripken Jr. and Tony Gwynn!

S14·E77 Core

Julianne Moore, Madonna, The Hold Steady

Jan 11, 2007

Videotape operator Tom Catusi apologizes for making a cheap shot at Mark McGwire; Madonna discusses her controversial adoption of a Malawian baby; Dave puts on a raincoat and promo

S14·E78 Core

Kristin Chenoweth, John Witherspoon, Josh Ritter

Jan 12, 2007

A Late Show Fun Fact: the actual Godzilla was only seven feet tall and was killed by Japanese soldiers within minutes; John Witherspoon describes a recent incident involving smokin

S14·E81 Core

Tina Fey, Terri and Bindi Irwin

Jan 17, 2007

Tina Fey discusses the Golden Globes and explains why she hates Los Angeles; escape artist "Donnie Glenn" balks at being sealed in a milk can filled with water; Terri & Bindi Irwin

S14·E82 Core

Harry Shearer, Vera Farmiga, Mat Kearney

Jan 18, 2007

Dave promotes the new, improved Late Show web site; "El Nino" (Gerard) drops by to take a bow; Vera Farmiga promotes "Breaking and Entering"; Mat Kearney performs "Nothing Left to

S14·E83 Core

Dan Rather, Tricia Helfer, Andy Kindler

Jan 19, 2007

Dave comments on this winter's damaged citrus crop by opening a carton of "Tropicana Just Rind"; Tricia Helfer of "Battlestar Galactica" fame promotes her upcoming Playboy pictoria

S14·E108 Core

Charles Grodin, Dan Naturman

Mar 2, 2007

Dave reminisces about his teen years and shares an antedote about a ruined fur coat; Charles Grodin promotes his one-minute commentaries on CBS Radio and shows off some of his hors

S14·E109 Core

Chris Rock, Sandra Oh, Amy Winehouse

Mar 12, 2007

Dave admits that he's never participated nor believes in Daylight Savings Time; Chris Rock promotes "I Think I Love My Wife"; Amy Winehouse performed "You Know I'm No Good."

S14·E125 Core

Kelly Ripa, Simon Pegg

Apr 16, 2007

Kelly Ripa, Simon Pegg, and Jim Short are the scheduled guests.

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