The BEST episodes of The Daily Show season 5

Every episode of The Daily Show season 5, ranked from best to worst by thousands of votes from fans of the show. The best episodes of The Daily Show season 5!

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: 9/22/2025Network: Comedy CentralStatus: Continuing
star
9.00
1 votes

#1 - Michael Moore

Season 5 - Episode 145 - Aired 11/9/2000

Tonight, documentary director Michael Moore promoting his TV series on Bravo called The Awful Truth.

Watch Now:Amazon
star
8.50
2 votes

#2 - Cynthia Nixon

Season 5 - Episode 1 - Aired 1/4/2000

star
8.50
2 votes

#3 - Richard Belzer

Season 5 - Episode 3 - Aired 1/6/2000

star
8.50
2 votes

#4 - Robbie Williams

Season 5 - Episode 2 - Aired 1/5/2000

star
7.00
27 votes

#5 - Shawn & Marlon Wayans

Season 5 - Episode 92 - Aired 7/17/2000

star
7.00
26 votes

#6 - Halle Berry

Season 5 - Episode 93 - Aired 7/18/2000

star
7.00
1 votes

#7 - Roger Daltrey

Season 5 - Episode 46 - Aired 4/10/2000

star
7.00
1 votes

#8 - Ben Stein

Season 5 - Episode 47 - Aired 4/11/2000

star
5.00
2 votes

#9 - Anna Paquin

Season 5 - Episode 88 - Aired 7/10/2000

star
0.00
0 votes

#10 - Kelli Williams

Season 5 - Episode 74 - Aired 6/6/2000

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0.00
0 votes

#11 - Sylvester Stallone

Season 5 - Episode 124 - Aired 9/27/2000

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0.00
0 votes

#12 - Michael Moore

Season 5 - Episode 75 - Aired 6/7/2000

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0.00
0 votes

#13 - When the Elderly Go on TV with Al Greenwood

Season 5 - Episode 76 - Aired 6/12/2000

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0.00
0 votes

#14 - Mark Curry

Season 5 - Episode 77 - Aired 6/13/2000

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0.00
0 votes

#15 - Jimmy Kimmel & Adam Carolla

Season 5 - Episode 78 - Aired 6/14/2000

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0.00
0 votes

#16 - Julie Brown

Season 5 - Episode 79 - Aired 6/15/2000

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0.00
0 votes

#17 - Heather Donahue

Season 5 - Episode 80 - Aired 6/19/2000

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0.00
0 votes

#18 - Joe Lockhart

Season 5 - Episode 81 - Aired 6/20/2000

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0.00
0 votes

#19 - Freddie Prinze Jr.

Season 5 - Episode 82 - Aired 6/21/2000

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0.00
0 votes

#20 - Alicia Silverstone

Season 5 - Episode 83 - Aired 6/22/2000

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0.00
0 votes

#21 - Cheri Oteri

Season 5 - Episode 84 - Aired 6/26/2000

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0.00
0 votes

#22 - Jeff Probst

Season 5 - Episode 85 - Aired 6/27/2000

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0.00
0 votes

#23 - Richie Sambora

Season 5 - Episode 86 - Aired 6/28/2000

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0.00
0 votes

#24 - John C. Reilly

Season 5 - Episode 87 - Aired 6/29/2000

star
0.00
0 votes

#25 - Barenaked Ladies

Season 5 - Episode 120 - Aired 9/20/2000