The BEST episodes of The Daily Show season 4

Every episode of The Daily Show season 4, ranked from best to worst by thousands of votes from fans of the show. The best episodes of The Daily Show season 4!

The Daily Show's intrepid news team dives into the biggest headlines of the day, providing fearless coverage, expert analysis, and no-nonsense commentary.

Last Updated: 8/5/2025Network: Comedy CentralStatus: Continuing
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#1 - Miss Piggy

Season 4 - Episode 85 - Aired 7/13/1999

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#2 - Natalie Portman

Season 4 - Episode 66 - Aired 5/26/1999

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#3 - David Cross

Season 4 - Episode 116 - Aired 9/16/1999

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#4 - Jamie Foxx

Season 4 - Episode 67 - Aired 5/27/1999

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#5 - Harry Connick Jr.

Season 4 - Episode 68 - Aired 6/7/1999

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#6 - Caroline Rhea

Season 4 - Episode 69 - Aired 6/8/1999

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#7 - Damon Wayans

Season 4 - Episode 70 - Aired 6/9/1999

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#8 - Timothy Hutton

Season 4 - Episode 71 - Aired 6/10/1999

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#9 - Mike Myers

Season 4 - Episode 72 - Aired 6/14/1999

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#10 - Rob Lowe

Season 4 - Episode 73 - Aired 6/15/1999

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#11 - Mike Myers

Season 4 - Episode 74 - Aired 6/16/1999

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#12 - Heather Graham

Season 4 - Episode 75 - Aired 6/17/1999

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#13 - Felicity Huffman

Season 4 - Episode 76 - Aired 6/21/1999

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#14 - Jimmy Kimmel

Season 4 - Episode 77 - Aired 6/22/1999

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#15 - Adam Sandler

Season 4 - Episode 78 - Aired 6/23/1999

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#16 - Richard Belzer

Season 4 - Episode 79 - Aired 6/24/1999

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#17 - Margaret Cho

Season 4 - Episode 80 - Aired 6/28/1999

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#18 - Scott Wolf

Season 4 - Episode 81 - Aired 6/29/1999

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#19 - Roseanne Barr

Season 4 - Episode 82 - Aired 6/30/1999

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#20 - Rob Schneider

Season 4 - Episode 83 - Aired 7/1/1999

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#21 - Andy Richter

Season 4 - Episode 117 - Aired 9/20/1999

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#22 - Thomas Gibson

Season 4 - Episode 56 - Aired 5/10/1999

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#23 - Marlee Matlin

Season 4 - Episode 47 - Aired 4/15/1999

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#24 - Sharon Lawrence

Season 4 - Episode 48 - Aired 4/19/1999

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#25 - Rob Estes

Season 4 - Episode 49 - Aired 4/20/1999