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The Best Episodes of Late Show with David Letterman Season 5

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!

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Episode Rankings

  1. #1 Fan Favorite
    Late Show with David Letterman Season 5 Episode 123 - Tom Hanks, Matt Medenweldt, Scott Weiland
    6.0/10(1 votes)

    S5:E123

    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.

    Director:Unknown
    Writer:Unknown

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  2. Late Show with David Letterman Season 5 Episode 1 - Terry Bradshaw, Carmen Electra, Eddie Brill
    0.0/10(0 votes)

    S5:E1

    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:Unknown
    Writer:Unknown

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  3. Late Show with David Letterman Season 5 Episode 2 - Steven Seagal, Brittany Starr, Beck
    0.0/10(0 votes)

    S5:E2

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

    Director:Unknown
    Writer:Unknown

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  4. Late Show with David Letterman Season 5 Episode 3 - Joan Lunden, Chris Rock, Fiona Apple
    0.0/10(0 votes)

    S5:E3

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

    Director:Unknown
    Writer:Unknown

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  5. Late Show with David Letterman Season 5 Episode 4 - Geena Davis, Martha Stewart, Robert Carlyle
    0.0/10(0 votes)

    S5:E4

    No description available

    Director:Unknown
    Writer:Unknown

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  6. Late Show with David Letterman Season 5 Episode 5 - Kevin Kline, Jamie Foxx, Sugar Ray
    0.0/10(0 votes)

    S5:E5

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

    Director:Unknown
    Writer:Unknown

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  7. Late Show with David Letterman Season 5 Episode 6 - Danny DeVito, Patrick Rafter, Tim McGraw
    0.0/10(0 votes)

    S5:E6

    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:Unknown
    Writer:Unknown

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  8. Late Show with David Letterman Season 5 Episode 7 - Salma Hayek, Joan Cusak, Louie Anderson
    0.0/10(0 votes)

    S5:E7

    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:Unknown
    Writer:Unknown

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  9. Late Show with David Letterman Season 5 Episode 8 - Noah Wylie, Damon Wayons, Missy "Misdemeanor" Elliot
    0.0/10(0 votes)

    S5:E8

    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:Unknown
    Writer:Unknown

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  10. Late Show with David Letterman Season 5 Episode 9 - Andie MacDowell, Cynthia Cooper, Nanci Griffith & Darius Rucker
    0.0/10(0 votes)

    S5:E9

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

    Director:Unknown
    Writer:Unknown

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  11. Late Show with David Letterman Season 5 Episode 10 - Jennifer Jason Leigh, Starr Jones, Bee Gees
    0.0/10(0 votes)

    S5:E10

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

    Director:Unknown
    Writer:Unknown

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  12. Late Show with David Letterman Season 5 Episode 11 - George Clooney, Bill Cosby
    0.0/10(0 votes)

    S5:E11

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

    Director:Unknown
    Writer:Unknown

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  13. Late Show with David Letterman Season 5 Episode 12 - Nicole Kidman, Gregory Hines, God's Property
    0.0/10(0 votes)

    S5:E12

    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:Unknown
    Writer:Unknown

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  14. Late Show with David Letterman Season 5 Episode 13 - Jennifer Lopez, Michael Lamonico, Bill Engvall
    0.0/10(0 votes)

    S5:E13

    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:Unknown
    Writer:Unknown

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  15. Late Show with David Letterman Season 5 Episode 14 - Alec Baldwin, Jonathan Lipnicki, Deana Carter
    0.0/10(0 votes)

    S5:E14

    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:Unknown
    Writer:Unknown

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  16. Late Show with David Letterman Season 5 Episode 15 - Kim Basinger, Ray Ramano, Jackson Browne
    0.0/10(0 votes)

    S5:E15

    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:Unknown
    Writer:Unknown

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  17. Late Show with David Letterman Season 5 Episode 16 - Fourth Anniversary Special
    0.0/10(0 votes)

    S5:E16

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

    Director:Unknown
    Writer:Unknown

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  18. Late Show with David Letterman Season 5 Episode 17 - Fran Drescher, Ryan Tripp, Brooks & Dunn
    0.0/10(0 votes)

    S5:E17

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

    Director:Unknown
    Writer:Unknown

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  19. Late Show with David Letterman Season 5 Episode 18 - Michael J. Fox, Sarah O'Hare, Patti Smith
    0.0/10(0 votes)

    S5:E18

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

    Director:Unknown
    Writer:Unknown

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  20. Late Show with David Letterman Season 5 Episode 19 - Cameron Diaz, Adam Arkin, Veniamin
    0.0/10(0 votes)

    S5:E19

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

    Director:Unknown
    Writer:Unknown

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  21. Late Show with David Letterman Season 5 Episode 20 - Matt Lauer, Ryan Kurlander, Sheryl Crow
    0.0/10(0 votes)

    S5:E20

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

    Director:Unknown
    Writer:Unknown

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  22. Late Show with David Letterman Season 5 Episode 21 - Elle MacPherson, Jon Tenney, Elvis Costello & the Fairfield Four
    0.0/10(0 votes)

    S5:E21

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

    Director:Unknown
    Writer:Unknown

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  23. Late Show with David Letterman Season 5 Episode 22 - Dan Aykroyd, Jack Hanna, Boyz II Men
    0.0/10(0 votes)

    S5:E22

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

    Director:Unknown
    Writer:Unknown

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  24. Late Show with David Letterman Season 5 Episode 23 - Bryant Gumbel, Harland Williams, Everclear
    0.0/10(0 votes)

    S5:E23

    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:Unknown
    Writer:Unknown

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  25. Late Show with David Letterman Season 5 Episode 24 - John Lithgow, Christy Turlington, Foo Fighters
    0.0/10(0 votes)

    S5:E24

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

    Director:Unknown
    Writer:Unknown

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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 6.0/10 from 1 votes. Written and directed by Unknown, it aired on April 3, 1998. This episode is rated 6.0 points higher than the second-best, "Terry Bradshaw, Carmen Electra, Eddie Brill".