The BEST episodes of Late Show with David Letterman season 21

Every episode of Late Show with David Letterman season 21, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Late Show with David Letterman season 21!

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: 6/6/2025Network: CBSStatus: Ended
Kevin Bacon; Pat McGann; Devon Avenue
star
8.00
1 votes

#1 - Kevin Bacon; Pat McGann; Devon Avenue

Season 21 - Episode 14 - Aired 1/24/2014

From "The Following", actor Kevin Bacon; stand-up comedy by Pat McGann; musical guests Devon Avenue.

Scarlett Johansson; John Grant
star
8.00
1 votes

#2 - Scarlett Johansson; John Grant

Season 21 - Episode 3 - Aired 1/8/2014

From "Captain America: The Winter Solider", actress Scarlett Johansson; musical guest John Grant.

George Clooney; Sting
star
7.51
55 votes

#3 - George Clooney; Sting

Season 21 - Episode 21 - Aired 2/4/2014

Dr. Phil McGraw; Danny Koker; Dum Dum Girls
star
7.50
2 votes

#4 - Dr. Phil McGraw; Danny Koker; Dum Dum Girls

Season 21 - Episode 18 - Aired 1/30/2014

TV host Dr. Phil McGraw; from "Counting Cars", TV personality Danny Koker; musical guests Dum Dum Girls.

Bill Murray; Eagulls
star
7.00
2 votes

#5 - Bill Murray; Eagulls

Season 21 - Episode 19 - Aired 1/31/2014

From "The Monuments Men", actor/comic Bill Murray; musical guests Eagulls.

Matt Damon; Lenny Kravitz
star
7.00
1 votes

#6 - Matt Damon; Lenny Kravitz

Season 21 - Episode 22 - Aired 2/5/2014

Lizzy Caplan, Sleeper Agent
star
7.00
27 votes

#7 - Lizzy Caplan, Sleeper Agent

Season 21 - Episode 96 - Aired 7/9/2014

Mariah Carey, Rick Harrison
star
6.10
27 votes

#8 - Mariah Carey, Rick Harrison

Season 21 - Episode 67 - Aired 5/7/2014

Sgt. Kyle J. White, Judy Greer, Dierks Bentley
star
0.00
0 votes

#9 - Sgt. Kyle J. White, Judy Greer, Dierks Bentley

Season 21 - Episode 77 - Aired 5/21/2014

Paul Rudd, Jeff Altman, John Doe
star
0.00
0 votes

#10 - Paul Rudd, Jeff Altman, John Doe

Season 21 - Episode 89 - Aired 6/19/2014

Donald Trump, Indianapolis 500 winner Ryan Hunter-Reay, Elizabeth Cook
star
0.00
0 votes

#11 - Donald Trump, Indianapolis 500 winner Ryan Hunter-Reay, Elizabeth Cook

Season 21 - Episode 78 - Aired 6/2/2014

Martin Short, John Oliver, Spanish Gold
star
0.00
0 votes

#12 - Martin Short, John Oliver, Spanish Gold

Season 21 - Episode 79 - Aired 6/3/2014

Anderson Cooper, Victor Espinoza, the Afghan Whigs
star
0.00
0 votes

#13 - Anderson Cooper, Victor Espinoza, the Afghan Whigs

Season 21 - Episode 80 - Aired 6/4/2014

Hugh Jackman, Joe List, Elvis Costello
star
0.00
0 votes

#14 - Hugh Jackman, Joe List, Elvis Costello

Season 21 - Episode 81 - Aired 6/5/2014

Kelsey Grammer, Willie Nelson
star
0.00
0 votes

#15 - Kelsey Grammer, Willie Nelson

Season 21 - Episode 82 - Aired 6/9/2014

Dave Chappelle, Laura Prepon, a Top Ten List presented by Miss USA, the Orwells
star
0.00
0 votes

#16 - Dave Chappelle, Laura Prepon, a Top Ten List presented by Miss USA, the Orwells

Season 21 - Episode 83 - Aired 6/10/2014

Christopher Walken, Janelle Monae
star
0.00
0 votes

#17 - Christopher Walken, Janelle Monae

Season 21 - Episode 84 - Aired 6/11/2014

Regis Philbin, Paul Morrissey, First Aid Kit
star
0.00
0 votes

#18 - Regis Philbin, Paul Morrissey, First Aid Kit

Season 21 - Episode 85 - Aired 6/12/2014

Susan Sarandon, Whitney Cummings, Angel Olsen, David Sanborn
star
0.00
0 votes

#19 - Susan Sarandon, Whitney Cummings, Angel Olsen, David Sanborn

Season 21 - Episode 86 - Aired 6/16/2014

Olivia Wilde, Shep Gordon, Empires
star
0.00
0 votes

#20 - Olivia Wilde, Shep Gordon, Empires

Season 21 - Episode 87 - Aired 6/17/2014

Dana Carvey, Ellie Kemper, Sam Smith
star
0.00
0 votes

#21 - Dana Carvey, Ellie Kemper, Sam Smith

Season 21 - Episode 88 - Aired 6/18/2014

Kiefer Sutherland, Adam Resnick, Benjamin Booker
star
0.00
0 votes

#22 - Kiefer Sutherland, Adam Resnick, Benjamin Booker

Season 21 - Episode 62 - Aired 4/30/2014

Kid scientists, Sarah Silverman, We Are Scientists
star
0.00
0 votes

#23 - Kid scientists, Sarah Silverman, We Are Scientists

Season 21 - Episode 76 - Aired 5/20/2014

Jack Hanna, Stephen Malkmus & the Jicks
star
0.00
0 votes

#24 - Jack Hanna, Stephen Malkmus & the Jicks

Season 21 - Episode 75 - Aired 5/19/2014

Lea Michele, Andy Kindler, Chromeo
star
0.00
0 votes

#25 - Lea Michele, Andy Kindler, Chromeo

Season 21 - Episode 74 - Aired 5/16/2014