Comedians The Funniest Observational Comedians of All Time  

Ranker Comedy
1.1k votes 217 voters 4.4k views 33 items

This list contains information about the best observational comedians, loosely ranked by user votes. The best observational comedians come in many forms. Some famous observational comedians find the funny in family life while other observational comedians say what we all are thinking. A few hilarious observational comedians have gone on to become some of the most successful stand-ups in the world.

Who will you find on this top observational comedians list? Jerry Seinfeld has to be at the top. Before he created and starred in the iconic “show about nothing” that was Seinfeld, the observational comic found the funny in the most mundane details of life in his stand-up act. Woody Allen is another one of the funniest observational comedians both on stage and on the big screen.

Whether he is analyzing relationships, race relations, or the ridiculousness of celebrities, Chris Rock is one of the most hilarious observational comedians in the business. Other funny stand-up comics featured on this best observational comedians list include Joan Rivers, George Carlin, and Dave Chappelle.

Which observational comedians do you think deserves the top spot on this list? Give the funniest comics a thumbs up and share some of your favorite jokes in the comments section.

list ordered by

1
47 24
George Carlin is listed (or ranked) 1 on the list The Funniest Observational Comedians of All Time
Dogma, Cars, Bill & Ted's Excellent Adventure

2
44 23
Bill Burr is listed (or ranked) 2 on the list The Funniest Observational Comedians of All Time
The Heat, Date Night, Walk of Shame

3
54 32
Jerry Seinfeld is listed (or ranked) 3 on the list The Funniest Observational Comedians of All Time
Seinfeld, Jerry Seinfeld: 'I'm Telling You for the Last Time', Comedian

4
54 33
Louis C.K. is listed (or ranked) 4 on the list The Funniest Observational Comedians of All Time
Late Night with Conan O'Brien, Louie, Louis C.K. Oh My God

5
39 23
Dave Chappelle is listed (or ranked) 5 on the list The Funniest Observational Comedians of All Time
Block Party, Half Baked, Chappelle's Show

6
33 19
Larry David is listed (or ranked) 6 on the list The Funniest Observational Comedians of All Time
Seinfeld, Curb Your Enthusiasm, The Three Stooges

7
25 13
Richard Pryor is listed (or ranked) 7 on the list The Funniest Observational Comedians of All Time
Richard Pryor: Live in Concert, Richard Pryor: Live on the Sunset Strip, Blazing Saddles

8
31 20
Chris Rock is listed (or ranked) 8 on the list The Funniest Observational Comedians of All Time
Chris Rock: Bigger & Blacker, Madagascar, Head of State

9
27 18
Jim Gaffigan is listed (or ranked) 9 on the list The Funniest Observational Comedians of All Time
It's Kind of a Funny Story, Away We Go, 17 Again

10
23 15
Mitch Hedberg is listed (or ranked) 10 on the list The Funniest Observational Comedians of All Time
Almost Famous, Lords of Dogtown, Los Enchiladas!

11
26 18
John Mulaney is listed (or ranked) 11 on the list The Funniest Observational Comedians of All Time
Saturday Night Live, Mulaney

12
24 18
Eddie Murphy is listed (or ranked) 12 on the list The Funniest Observational Comedians of All Time
Beverly Hills Cop, Trading Places, Coming to America

13
21 16
Jim Jefferies is listed (or ranked) 13 on the list The Funniest Observational Comedians of All Time
Legit, Down and Dirty with Jim Norton, Jim Jefferies: I Swear to God

14
15 11
Norm Macdonald is listed (or ranked) 14 on the list The Funniest Observational Comedians of All Time
Dirty Work, Billy Madison, Saturday Night Live

15
14 10
Don Rickles is listed (or ranked) 15 on the list The Funniest Observational Comedians of All Time
Toy Story, Toy Story 3, Toy Story 2

16
15 13
Demetri Martin is listed (or ranked) 16 on the list The Funniest Observational Comedians of All Time
Late Night with Conan O'Brien, Demetri Martin. Person., Important Things with Demetri Martin

17
12 10
Brian Regan is listed (or ranked) 17 on the list The Funniest Observational Comedians of All Time
Dr. Katz, Professional Therapist, Shorties Watchin' Shorties

18
18 17
Woody Allen is listed (or ranked) 18 on the list The Funniest Observational Comedians of All Time
Annie Hall, Midnight in Paris, Vicky Cristina Barcelona

19
17 17
Bill Hicks is listed (or ranked) 19 on the list The Funniest Observational Comedians of All Time
Comedy's Dirtiest Dozen, Bill Hicks: Sane Man, Bill Hicks Live: Satirist

20
4 3
Ricky Gervais is listed (or ranked) 20 on the list The Funniest Observational Comedians of All Time
italosouza added The Office, The Invention of Lying, Cemetery Junction

21
12 12
Billy Connolly is listed (or ranked) 21 on the list The Funniest Observational Comedians of All Time
Brave, The Last Samurai, The Boondock Saints

22
12 13
Gabriel Iglesias is listed (or ranked) 22 on the list The Funniest Observational Comedians of All Time
Magic Mike, All That, Planes

23
7 8
David Brenner is listed (or ranked) 23 on the list The Funniest Observational Comedians of All Time
Worth Winning, Snip

24
15 17
Joan Rivers is listed (or ranked) 24 on the list The Funniest Observational Comedians of All Time
Fashion Police, The Joan Rivers Show, The Joan Rivers Show

25
6 7
Kathleen Madigan is listed (or ranked) 25 on the list The Funniest Observational Comedians of All Time
Alexandre Lussier added Last Comic Standing, Kathleen Madigan: Gone Madigan, The Great Debate