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 by thousands of votes from fans of the show. The best episodes of Late Show with David Letterman season 5!

“Late Show with David Letterman” is 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: 4/6/2024Network: CBSStatus: Ended
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Show #1003
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#1 - Show #1003

Season 5 - Episode 141 - Aired 5/6/1998

Biff tries out tobacco juice spin art; Dave shows a clip from last night's show in which he mixed up "Viagra" with "Niagara"; Biff teaches Sally Field how to spit tobacco juice.

Directors: Jerry Foley
Show #0991
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#2 - Show #0991

Season 5 - Episode 129 - Aired 4/20/1998

Dave announces the birth of Jerry Foley's son; after showing footage from last year of Rob Burnett unwittingly scaring his young daughter in a Easter Bunny suit, he tries on a different outfit with more or less the same results; Harmony Korine almost says something coherent while being interviewed about his new book, which he wouldn't particularly recommend, so Dave tells him to go back to his hotel and take a shower.

Directors: Jerry Foley
Show #0992
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#3 - Show #0992

Season 5 - Episode 130 - Aired 4/21/1998

The Guy Not on Fire announces that he is now available for commercials and endorsements, and later in the show he is seen in an ad for Sizzler. Also, Danny DeVito comes out onstage twice to protest Dave's jokes about him being a car hood ornament.

Directors: Jerry Foley
Show #0993
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#4 - Show #0993

Season 5 - Episode 131 - Aired 4/22/1998

The Guy Not on Fire appears in his first paid ad (for Elite Computers); a chat with Jason Alexander is interrupted by another inane special report by Alan Richardson; Steve Earle and the Dukes perform "I Still Carry You Around."

Show #0994
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#5 - Show #0994

Season 5 - Episode 132 - Aired 4/23/1998

"Know Your Current Events" is interrupted so that The Man Not on Fire can pitch the Biore® self-heating mask. Later in the show, Dave admits that he's on a guilt trip for bumping an audience member for the shameless plug.

Directors: Jerry Foley
Show #0995
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#6 - Show #0995

Season 5 - Episode 133 - Aired 4/24/1998

Amongst the festivities of "Chicago Night": Jerry Springer's bouncers stand on opposite sides of the stage; The Man Not on Fire appears in an ad for Gold Coast Drugs; the Top Ten home office is temporarily moved to nearby Schaumberg, Illinois; local blues singer (and frequent guest) Taj Mahal presents the Top Ten; Bob Borden goes on a frantic pursuit through the Windy City attempting to get an interview with Oprah.

Directors: Jerry Foley
Show #0996
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#7 - Show #0996

Season 5 - Episode 134 - Aired 4/27/1998

Dave persuades an audience member named Gary to shave off his beard; The man who was on fire, then wasn't and is now on fire again promotes Kraus Chiropractic in Iowa; Gary orders a sandwich at Hello Deli; Dave and recent NFL draft pick Ryan Leaf throw footballs at a manhole.

Directors: Jerry Foley
Show #0997
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#8 - Show #0997

Season 5 - Episode 135 - Aired 4/28/1998

Willie "Blue Moon" Watts sits in on pedal guitar; Dave announces that there have been some technical difficulties they may prevent Johnny Depp from appearing on the 1000th show later in the week; The Man on Fire sings the praises of Feline Pine kitty litter.

Directors: Jerry Foley
Show #0998
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#9 - Show #0998

Season 5 - Episode 136 - Aired 4/29/1998

The latest roll call suggests that The Guy on Fire has officially sold out when he runs across the stage (in flames, of course) holding a sign for Highland Metals, Inc.

Directors: Jerry Foley
Show #0999
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#10 - Show #0999

Season 5 - Episode 137 - Aired 4/30/1998

A monkey assumes power in the control room, while the Top Ten is interrupted by Antoine's Po' Boys and Deli spokesperson The Man on Fire.

Directors: Jerry Foley
Show #1000
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#11 - Show #1000

Season 5 - Episode 138 - Aired 5/1/1998

Tonight's "Stupid Human Tricks": Richard Anthony of Ontario reaches back over his shoulder and gives himself a wedgie; John Rites of Nebraska fits three McDonald's burgers into his mouth; and Mike Garcia and Craig Love of Milwaukee do an impression of a helicopter as one spins on the other's head; Gene Siskel makes his first public appearance since undergoing brain surgery that April; Dave announces Johnny Depp cancelled due to the technical difficulties from earlier in the week, and Paul goes on a tirade about it.

Show #1001
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#12 - Show #1001

Season 5 - Episode 139 - Aired 5/4/1998

Maynard Ferguson sits in again; Paul runs the Kentucky Derby; Dave shows a microphone plaque he got from the staff.

Directors: Jerry Foley
Show #1002
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#13 - Show #1002

Season 5 - Episode 140 - Aired 5/5/1998

The cast of the faux musical "Homecoming" performs a show-stopping number. Also, Trisha Yearwood performs "Never Let You Go Again."

Directors: Jerry Foley
Show #0990
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#14 - Show #0990

Season 5 - Episode 128 - Aired 4/10/1998

During CBS Mailbag, a viewer asks if Dave has any plans to air his show from the space shuttle. Somehow as a response, astronaut Buzz Aldrin is seen hitting golfballs on the theatre roof.

Directors: Jerry Foley
Show #1004
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#15 - Show #1004

Season 5 - Episode 142 - Aired 5/7/1998

Dave promotes his new talk show summer camp, while Green Day performs "King for a Day."

Directors: Jerry Foley
Show #1005
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#16 - Show #1005

Season 5 - Episode 143 - Aired 5/8/1998

Biff goes to Texas to learn to be a cowboy, and to make tonight's audience (residents of Houston) feel more at home, Lyle Lovett shows up to sing an old Hank Williams song, with Biff riding his horse onstage.

Directors: Jerry Foley
Show #1006
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#17 - Show #1006

Season 5 - Episode 144 - Aired 5/11/1998

Dave visits a group of sailors on the audience, and one of them does a push-up onstage; Dave shows the audience today's (bogus) edition of The Family Circus; Faith Hill performs "This Kiss."

Directors: Jerry Foley
Show #1007
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#18 - Show #1007

Season 5 - Episode 145 - Aired 5/12/1998

Dave shows another bogus "Family Circus" cartoon; Paul is discovered cheering on Hanson with a small army of teenyboppers outside.

Directors: Jerry Foley
Show #1008
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#19 - Show #1008

Season 5 - Episode 146 - Aired 5/13/1998

Dave notices the standby audience really has nothing to do, so makes them do a jigsaw puzzle. When they finish it at the end of the show, we see that it's an image of Al Chez.

Directors: Jerry Foley
Show #1009
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#20 - Show #1009

Season 5 - Episode 147 - Aired 5/14/1998

Dave gripes about the eight-minute late start for the show tonight due to golf coverage. Rapidly becoming despondent, he picks up a bottle of tequila and tosses back a few at the desk. Also, Dave mentions that the CBS program Diagnosis Murder had the unfortunate distinction of airing a brand new episode up against the Seinfeld finale, and shows a clip that proves that they were phoning it in.

Directors: Jerry Foley
Show #1010
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#21 - Show #1010

Season 5 - Episode 148 - Aired 5/15/1998

Continuing a sweeps period trend of having the audience represent a different city, Dave greets 700+ residents of New Orleans, Louisiana. Keeping up with the theme, Mayor Mark Morial presents Paul with a key to the city, Na'lens native John Goodman presents the Top Ten, and Biff visits Bourbon Street.

Directors: Jerry Foley
Show #1011
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#22 - Show #1011

Season 5 - Episode 149 - Aired 5/18/1998

The outside cam peers through the window of Dave's office to show the world a very hideous billboard promoting the sitcom Friends. Matthew Perry drops by to vandalize the advertisement.

Directors: Jerry Foley
Show #1012
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#23 - Show #1012

Season 5 - Episode 150 - Aired 5/19/1998

The outside cam returns to the Friends ad that Matthew Perry wrecked last night, and Dave explains why he shouldn't be sued; Rob Burnett draws another doodle of Dave's lawyers; the Top Ten list is interrupted by the office manager in Wahoo, Nebraska (voice of Charles Grodin).

Directors: Jerry Foley
Show #1013
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#24 - Show #1013

Season 5 - Episode 151 - Aired 5/20/1998

Biff reports from a Bulls-Pacers playoff game; teen actress Scarlett Johansson promotes The Horse Whisperer; Rob Burnett is dressed to the nines tonight, so Dave asks him to host the last twenty minutes of the show.

Directors: Jerry Foley
Show #1014
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#25 - Show #1014

Season 5 - Episode 152 - Aired 5/21/1998

A hairstylist that appeared in tonight's "Know Your Current Events" cuts Dave's hair for twenty bucks. He later gives her a $1000 tip.

Directors: Jerry Foley