The BEST episodes of Late Night with Conan O'Brien season 6

Every episode of Late Night with Conan O'Brien season 6, ranked from best to worst by thousands of votes from fans of the show. The best episodes of Late Night with Conan O'Brien season 6!

Stepping into the late-late slot vacated by David Letterman, Conan O'Brien stars in a show that far outdoes its nocturnal competition in sheer strangeness. Along with the standard interviews and musical guests typical of late-night talk shows, this incarnation of "Late Night" makes frequent use of creatively odd walk-on characters and frequent visits from celebrity guests, real and imagined.

Last Updated: 6/23/2025Network: NBCStatus: Ended
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#1 - Hugh Grant, Esther Canadas, Louis C.K.

Season 6 - Episode 160 - Aired 8/19/1999

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#2 - Thane Maynard, Dweezil & Ahmet Zappa, Greg Behrendt

Season 6 - Episode 95 - Aired 3/31/1999

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#3 - Harvey Keitel, Michael Rapaport, Patty Griffin

Season 6 - Episode 113 - Aired 5/7/1999

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#4 - Jackie Chan, Diane Lane, Al Kooper

Season 6 - Episode 96 - Aired 4/1/1999

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#5 - Kevin Pollak, Josh Charles, Collective Soul

Season 6 - Episode 97 - Aired 4/2/1999

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#6 - Lyle Lovett, David Brenner, Amy Sedaris

Season 6 - Episode 98 - Aired 4/6/1999

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#7 - David Arquette, Jerry O'Connell, Susan Tedeschi

Season 6 - Episode 99 - Aired 4/7/1999

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#8 - Will Ferrell, Jennifer Esposito, Mike Lupica

Season 6 - Episode 100 - Aired 4/8/1999

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#9 - Jay Mohr, Jerry Springer, Citizen King

Season 6 - Episode 101 - Aired 4/9/1999

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#10 - Martha Stewart, David Blaine, Todd Barry

Season 6 - Episode 102 - Aired 4/13/1999

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#11 - Liv Tyler, Tim Meadows, Juvenile

Season 6 - Episode 103 - Aired 4/14/1999

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#12 - Evander Holyfield, Marc Maron, Latin Playboys

Season 6 - Episode 104 - Aired 4/15/1999

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#13 - Chris O'Donnell, Megan Mullally, David Feldman

Season 6 - Episode 105 - Aired 4/16/1999

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#14 - Matt Lauer, Seth Green, Sugar Ray

Season 6 - Episode 106 - Aired 4/27/1999

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#15 - George Stephanopoulos, Ana Gasteyer, Paula Cale

Season 6 - Episode 107 - Aired 4/28/1999

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#16 - Michael J. Fox, Kevin James, Billy Burr

Season 6 - Episode 108 - Aired 4/29/1999

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#17 - Matthew Broderick, Michael Moore, Godsmack

Season 6 - Episode 109 - Aired 4/30/1999

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#18 - Al Roker, Louis C.K., Madness

Season 6 - Episode 110 - Aired 5/4/1999

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#19 - Aidan Quinn, Christa Miller, Greg Giraldo

Season 6 - Episode 111 - Aired 5/5/1999

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#20 - Julianne Moore, Reese Witherspoon, Scott Dikkers

Season 6 - Episode 112 - Aired 5/6/1999

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#21 - Paul Reiser, Chris Kattan, Old 97's

Season 6 - Episode 114 - Aired 5/11/1999

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#22 - Mark Wahlberg, Wendie Malick, Gene Pompa

Season 6 - Episode 84 - Aired 3/4/1999

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#23 - Colin Quinn, Congressman Barney Frank

Season 6 - Episode 50 - Aired 12/23/1998

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#24 - Charles Grodin, Ana Gasteyer, Ozomatli

Season 6 - Episode 52 - Aired 12/30/1998

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#25 - Tyra Banks, David Alan Grier, The Sklar Brothers

Season 6 - Episode 64 - Aired 1/21/1999