As of July 2026, Late Show with David Letterman Season 5 aired in 1997 with 203 episodes. Full episode guide and where to watch below.
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Late Show with David Letterman Season 5

1997 203 Episodes Talk · Comedy ⭐ 6/10

Late Show with David Letterman Season 5 has quietly become one of the more dependable comedies currently available. The show says what it needs to say in a single season, no filler. 169 people have weighed in on TMDB, and the verdict leans heavily positive. Watch it for David Letterman — stay for everyone else around them. Available now — press play and find out why people keep recommending it.

There is a reason Late Show with David Letterman Season 5 keeps coming up in conversation. The jokes in Late Show with David Letterman Season 5 land because the characters underneath them are worth caring about. Season 5 of Late Show with David Letterman includes 203 episodes. It aired from September 1997 to August 1998. This season stars David Letterman, Paul Shaffer and Alan Kalter. David Letterman and Paul Shaffer lead a cast that brings real weight to the material. It was aired in 1997. What keeps Late Show with David Letterman Season 5 from feeling disposable is a cast that clearly understands the material better than the format usually demands. It knows exactly what it is, and does not try to be anything else.

Comedy fans looking for a reliably funny watch will find it in Late Show with David Letterman Season 5. It rewards viewers regardless of what else is in their watch history. Short enough to finish in a weekend, substantial enough to feel satisfying. David Letterman's comic timing carries it through its weaker moments. The kind of comedy you recommend to someone who claims they do not watch much.

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🎬 Late Show with David Letterman Season 5 — Episode Guide

E1
Terry Bradshaw, Carmen Electra, Eddie Brill
1997-09-01
Dave shows highlights from the annual Labor Day staff cookout on 53rd Street; Terry Bradshaw and stagehand Corky Ramirez both inexplicably break into song.
E2
Steven Seagal, Brittany Starr, Beck
1997-09-02
Warren is caught watching tennis on TV; Dave harasses teen talk show host John Hall; Beck performs ""Devil's Haircut.""
E3
Joan Lunden, Chris Rock, Fiona Apple
1997-09-03
Viewers at home receive the rare opportunity to see the new audience orientation tape (starring Leonard Tepper). Later, Fiona Apple performs ""Criminal.""
E4
Geena Davis, Martha Stewart, Robert Carlyle
1997-09-04
E5
Kevin Kline, Jamie Foxx, Sugar Ray
1997-09-05
On Warren's last night filling in for Paul, he receives a ""Deputy of Comedy"" badge. Later, Sugar Ray performs ""Fly.""
E6
Danny DeVito, Patrick Rafter, Tim McGraw
1997-09-08
Paul returns from filming ""Blues Brothers 2000"" with a shaved head. Meanwhile, Dave, Biff, Regis, Al Roker, and Bob Barker harass people in Central Park.
E7
Salma Hayek, Joan Cusak, Louie Anderson
1997-09-09
Dave calls the pay phone island outside so that an unsuspecting tourist could participate in a comedy skit. When nobody picks up a phone, Dave goes on the street and invites a guy from Vermont to perform a musical number with Tony Randall.
E8
Noah Wylie, Damon Wayons, Missy "Misdemeanor" Elliot
1997-09-10
Dave is so fascinated by Paul's shaved head (introduced last night) that he has to talk about it at the beginning of the show.
E9
Andie MacDowell, Cynthia Cooper, Nanci Griffith & Darius Rucker
1997-09-11
Paul writes a song for a trucker who participated in ""Know Your Current Events,"" while Dave chats with WNBA MVP Cynthia Cooper.
E10
Jennifer Jason Leigh, Starr Jones, Bee Gees
1997-09-12
Dave chats with CBS star ""Steve Urkel"" (Gerard), while Star Jones plugs ""The View.""
E11
George Clooney, Bill Cosby
1997-09-22
Dave listens to the philosophies of second-graders in ""Dave Talks to Kids""; George Clooney promotes ""The Peacemaker.""
E12
Nicole Kidman, Gregory Hines, God's Property
1997-09-23
Biff delivers a housewarming gift to a Hooters franchise that just opened, and they send back buffalo wings. Later, an NBC nurse tends to Nicole Kidman's cold.
E13
Jennifer Lopez, Michael Lamonico, Bill Engvall
1997-09-24
Dave discusses aerosol cheese with last minute guest Chef Michael Lomonaco who says, ""It's great when you're driving, actually. You get a little squirt when you're driving.""
E14
Alec Baldwin, Jonathan Lipnicki, Deana Carter
1997-09-25
Richard Simmons interupts ""Know Your Current Events""; Drew Carey presents ""Top Ten Signs You Work in a Bad Office""; 7-year-old Jonathan Lipnicki promotes his new sitcom, ""Meego.""
E15
Kim Basinger, Ray Ramano, Jackson Browne
1997-09-26
In a return to the popular theme nights of yore, the entire LATE SHOW audience consists of freshmen from NYU. During the show, Candice Bergen presents a special college-themed Top Ten list.
E16
Fourth Anniversary Special
1997-09-29
Dave shows some of his favorite remotes, segments, and comedy clips from the first four years of ""The Late Show.""
E17
Fran Drescher, Ryan Tripp, Brooks & Dunn
1997-09-29
Bob Borden finally gets to meet Jaleel ""Urkel"" White, while Paul composes a musical number about pastries that resemble celebrities.
E18
Michael J. Fox, Sarah O'Hare, Patti Smith
1997-09-30
Dave gives a local named Tom Worzall ten seconds of air time, then chats with Wonderbra model Sarah O'Hare.
E19
Cameron Diaz, Adam Arkin, Veniamin
1997-10-01
Cameron Diaz promotes ""A Life Less Ordinary,"" while the famed contortionist Veniamin does a demonstration.
E20
Matt Lauer, Ryan Kurlander, Sheryl Crow
1997-10-02
Dave comments on the Yankees playoff chances, then chats with new ""Today"" co-host Matt Lauer.

🎭 Cast of Late Show with David Letterman Season 5

David Letterman
David Letterman
Self - Host
Paul Shaffer
Paul Shaffer
Self -Musical Director
AK
Alan Kalter
Self - Announcer (voice)

📋 All Seasons of Late Show with David Letterman

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