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The Best Episodes of Late Show with David Letterman Season 5

Genres:TalkComedy
Network:CBS

Every episode of Late Show with David Letterman Season 5 ranked from best to worst. Discover the Best Episodes of Late Show with David Letterman Season 5!

Late Show with David Letterman is an American late-night talk show hosted by David Letterman on CBS. The show debuted on August 30, 1993, and...
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  • Tom Hanks, Matt Medenweldt, Scott Weiland
    6.0/10(1)
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    #1 - Tom Hanks, Matt Medenweldt, Scott Weiland

    Season 5 Episode 123

    Aired 4/3/1998

    Tom Hanks interrupts the monologue because he and Dave are dressed alike; throughout the night, spelling bee champ Edmund Gillette stands next to Rob's desk and spells words; during Mailbag, Alan Kalter reacts badly to a letter asking if he's a freak by visiting the letter-writer (Jay Johnson) and punching in his face; Tom gets a new suit.

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  • Terry Bradshaw, Carmen Electra, Eddie Brill
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    #2 - Terry Bradshaw, Carmen Electra, Eddie Brill

    Season 5 Episode 1

    Aired 9/1/1997

    Dave shows highlights from the annual Labor Day staff cookout on 53rd Street; Terry Bradshaw and stagehand Corky Ramirez both inexplicably break into song.

    Director: N/A

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  • Steven Seagal, Brittany Starr, Beck
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    #3 - Steven Seagal, Brittany Starr, Beck

    Season 5 Episode 2

    Aired 9/2/1997

    Warren is caught watching tennis on TV; Dave harasses teen talk show host John Hall; Beck performs ""Devil's Haircut.""

    Director: N/A

    Writer: N/A

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  • Joan Lunden, Chris Rock, Fiona Apple
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    #4 - Joan Lunden, Chris Rock, Fiona Apple

    Season 5 Episode 3

    Aired 9/3/1997

    Viewers at home receive the rare opportunity to see the new audience orientation tape (starring Leonard Tepper). Later, Fiona Apple performs ""Criminal.""

    Director: N/A

    Writer: N/A

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  • Geena Davis, Martha Stewart, Robert Carlyle
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    #5 - Geena Davis, Martha Stewart, Robert Carlyle

    Season 5 Episode 4

    Aired 9/4/1997

    No description available

    Director: N/A

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  • Kevin Kline, Jamie Foxx, Sugar Ray
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    #6 - Kevin Kline, Jamie Foxx, Sugar Ray

    Season 5 Episode 5

    Aired 9/5/1997

    On Warren's last night filling in for Paul, he receives a ""Deputy of Comedy"" badge. Later, Sugar Ray performs ""Fly.""

    Director: N/A

    Writer: N/A

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  • Danny DeVito, Patrick Rafter, Tim McGraw
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    #7 - Danny DeVito, Patrick Rafter, Tim McGraw

    Season 5 Episode 6

    Aired 9/8/1997

    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.

    Director: N/A

    Writer: N/A

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  • Salma Hayek, Joan Cusak, Louie Anderson
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    #8 - Salma Hayek, Joan Cusak, Louie Anderson

    Season 5 Episode 7

    Aired 9/9/1997

    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.

    Director: N/A

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  • Noah Wylie, Damon Wayons, Missy "Misdemeanor" Elliot
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    #9 - Noah Wylie, Damon Wayons, Missy "Misdemeanor" Elliot

    Season 5 Episode 8

    Aired 9/10/1997

    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.

    Director: N/A

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  • Andie MacDowell, Cynthia Cooper, Nanci Griffith & Darius Rucker
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    #10 - Andie MacDowell, Cynthia Cooper, Nanci Griffith & Darius Rucker

    Season 5 Episode 9

    Aired 9/11/1997

    Paul writes a song for a trucker who participated in ""Know Your Current Events,"" while Dave chats with WNBA MVP Cynthia Cooper.

    Director: N/A

    Writer: N/A

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  • Jennifer Jason Leigh, Starr Jones, Bee Gees
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    #11 - Jennifer Jason Leigh, Starr Jones, Bee Gees

    Season 5 Episode 10

    Aired 9/12/1997

    Dave chats with CBS star ""Steve Urkel"" (Gerard), while Star Jones plugs ""The View.""

    Director: N/A

    Writer: N/A

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  • George Clooney, Bill Cosby
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    #12 - George Clooney, Bill Cosby

    Season 5 Episode 11

    Aired 9/22/1997

    Dave listens to the philosophies of second-graders in ""Dave Talks to Kids""; George Clooney promotes ""The Peacemaker.""

    Director: N/A

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  • Nicole Kidman, Gregory Hines, God's Property
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    #13 - Nicole Kidman, Gregory Hines, God's Property

    Season 5 Episode 12

    Aired 9/23/1997

    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.

    Director: N/A

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  • Jennifer Lopez, Michael Lamonico, Bill Engvall
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    #14 - Jennifer Lopez, Michael Lamonico, Bill Engvall

    Season 5 Episode 13

    Aired 9/24/1997

    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.""

    Director: N/A

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  • Alec Baldwin, Jonathan Lipnicki, Deana Carter
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    #15 - Alec Baldwin, Jonathan Lipnicki, Deana Carter

    Season 5 Episode 14

    Aired 9/25/1997

    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.""

    Director: N/A

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  • Kim Basinger, Ray Ramano, Jackson Browne
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    #16 - Kim Basinger, Ray Ramano, Jackson Browne

    Season 5 Episode 15

    Aired 9/26/1997

    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.

    Director: N/A

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  • Fourth Anniversary Special
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    #17 - Fourth Anniversary Special

    Season 5 Episode 16

    Aired 9/29/1997

    Dave shows some of his favorite remotes, segments, and comedy clips from the first four years of ""The Late Show.""

    Director: N/A

    Writer: N/A

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  • Fran Drescher, Ryan Tripp, Brooks & Dunn
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    #18 - Fran Drescher, Ryan Tripp, Brooks & Dunn

    Season 5 Episode 17

    Aired 9/29/1997

    Bob Borden finally gets to meet Jaleel ""Urkel"" White, while Paul composes a musical number about pastries that resemble celebrities.

    Director: N/A

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  • Michael J. Fox, Sarah O'Hare, Patti Smith
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    #19 - Michael J. Fox, Sarah O'Hare, Patti Smith

    Season 5 Episode 18

    Aired 9/30/1997

    Dave gives a local named Tom Worzall ten seconds of air time, then chats with Wonderbra model Sarah O'Hare.

    Director: N/A

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  • Cameron Diaz, Adam Arkin, Veniamin
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    #20 - Cameron Diaz, Adam Arkin, Veniamin

    Season 5 Episode 19

    Aired 10/1/1997

    Cameron Diaz promotes ""A Life Less Ordinary,"" while the famed contortionist Veniamin does a demonstration.

    Director: N/A

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  • Matt Lauer, Ryan Kurlander, Sheryl Crow
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    #21 - Matt Lauer, Ryan Kurlander, Sheryl Crow

    Season 5 Episode 20

    Aired 10/2/1997

    Dave comments on the Yankees playoff chances, then chats with new ""Today"" co-host Matt Lauer.

    Director: N/A

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  • Elle MacPherson, Jon Tenney, Elvis Costello & the Fairfield Four
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    #22 - Elle MacPherson, Jon Tenney, Elvis Costello & the Fairfield Four

    Season 5 Episode 21

    Aired 10/3/1997

    Dave shows (bogus) NASA footage of Mir; the Dutch Mariachis sing ""Happy Birthday"" to Biff.

    Director: N/A

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  • Dan Aykroyd, Jack Hanna, Boyz II Men
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    #23 - Dan Aykroyd, Jack Hanna, Boyz II Men

    Season 5 Episode 22

    Aired 10/6/1997

    Dave and Paul visit the ""International Hair Forum""; Dan Aykroyd promotes ""Soul Man"" and plays the harmonica.

    Director: N/A

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  • Bryant Gumbel, Harland Williams, Everclear
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    #24 - Bryant Gumbel, Harland Williams, Everclear

    Season 5 Episode 23

    Aired 10/7/1997

    Joe G. stars in the new crime drama ""Joey Ventura,"" and clips from the show are scattered throughout the night; Dave gives Paul crap for bumping into a cameraman; Bryant Gumbel promotes his soon-to-debut news program.

    Director: N/A

    Writer: N/A

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  • John Lithgow, Christy Turlington, Foo Fighters
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    #25 - John Lithgow, Christy Turlington, Foo Fighters

    Season 5 Episode 24

    Aired 10/8/1997

    Dave watches leaves turn and nails dry, and an audience member's receives and smokes his first cigar.

    Director: N/A

    Writer: N/A

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Season 5 Ratings Summary

"Tom Hanks, Matt Medenweldt, Scott Weiland" is the best rated episode of "Late Show with David Letterman" season 5. It scored 6/10 based on 1 votes. Directed by N/A and written by N/A, it aired on 4/3/1998. This episode is rated NaN points higher than the second-best, "Terry Bradshaw, Carmen Electra, Eddie Brill".