Comedians The Funniest Observational Comedians of All Time  

Ranker Comedy
734 votes 135 voters 2.3k views 32 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.

1
31 14
George Carlin is listed (or ranked) 1 on the list The Funniest Observational Comedians of All Time
George Carlin Dogma, Cars, Bill & Ted's Excellent Adventure

2
23 9
Bill Burr is listed (or ranked) 2 on the list The Funniest Observational Comedians of All Time
Bill Burr The Heat, Date Night, Walk of Shame

3
34 21
Jerry Seinfeld is listed (or ranked) 3 on the list The Funniest Observational Comedians of All Time
Jerry Seinfeld Seinfeld, Jerry Seinfeld: 'I'm Telling You for the Last Time', Comedian

4
26 14
Dave Chappelle is listed (or ranked) 4 on the list The Funniest Observational Comedians of All Time
Dave Chappelle Block Party, Half Baked, Chappelle's Show

5
33 20
Louis C.K. is listed (or ranked) 5 on the list The Funniest Observational Comedians of All Time
Louis C.K. Late Night with Conan O'Brien, Louie, Louis C.K. Oh My God

6
17 8
Mitch Hedberg is listed (or ranked) 6 on the list The Funniest Observational Comedians of All Time
Mitch Hedberg Almost Famous, Lords of Dogtown, Los Enchiladas!

7
23 13
Chris Rock is listed (or ranked) 7 on the list The Funniest Observational Comedians of All Time
Chris Rock Chris Rock: Bigger & Blacker, Madagascar, Head of State

8
15 7
Richard Pryor is listed (or ranked) 8 on the list The Funniest Observational Comedians of All Time
Richard Pryor Richard Pryor: Live in Concert, Richard Pryor: Live on the Sunset Strip, Blazing Saddles

9
21 13
Larry David is listed (or ranked) 9 on the list The Funniest Observational Comedians of All Time
Larry David Seinfeld, Curb Your Enthusiasm, The Three Stooges

10
16 10
John Mulaney is listed (or ranked) 10 on the list The Funniest Observational Comedians of All Time
John Mulaney Saturday Night Live, Mulaney

11
19 13
Eddie Murphy is listed (or ranked) 11 on the list The Funniest Observational Comedians of All Time
Eddie Murphy Beverly Hills Cop, Trading Places, Coming to America

12
13 8
Bill Hicks is listed (or ranked) 12 on the list The Funniest Observational Comedians of All Time
Bill Hicks Comedy's Dirtiest Dozen, Bill Hicks: Sane Man, Bill Hicks Live: Satirist

13
14 8
Jim Jefferies is listed (or ranked) 13 on the list The Funniest Observational Comedians of All Time
Jim Jefferies Legit, Down and Dirty with Jim Norton, Jim Jefferies: I Swear to God

14
17 13
Jim Gaffigan is listed (or ranked) 14 on the list The Funniest Observational Comedians of All Time
Jim Gaffigan It's Kind of a Funny Story, Away We Go, 17 Again

15
10 7
Billy Connolly is listed (or ranked) 15 on the list The Funniest Observational Comedians of All Time
Billy Connolly Brave, The Last Samurai, The Boondock Saints

16
5 2
Kathleen Madigan is listed (or ranked) 16 on the list The Funniest Observational Comedians of All Time
Alexandre Lussier added Kathleen Madigan Last Comic Standing, Kathleen Madigan: Gone Madigan, The Great Debate

17
10 8
Demetri Martin is listed (or ranked) 17 on the list The Funniest Observational Comedians of All Time
Demetri Martin Late Night with Conan O'Brien, Demetri Martin. Person., Important Things with Demetri Martin

18
9 8
Don Rickles is listed (or ranked) 18 on the list The Funniest Observational Comedians of All Time
Don Rickles Toy Story, Toy Story 3, Toy Story 2

19
8 7
Norm Macdonald is listed (or ranked) 19 on the list The Funniest Observational Comedians of All Time
Norm Macdonald Dirty Work, Billy Madison, Saturday Night Live

20
7 6
Brian Regan is listed (or ranked) 20 on the list The Funniest Observational Comedians of All Time
Brian Regan Dr. Katz, Professional Therapist, Shorties Watchin' Shorties

21
13 13
Joan Rivers is listed (or ranked) 21 on the list The Funniest Observational Comedians of All Time
Joan Rivers Fashion Police, The Joan Rivers Show, The Joan Rivers Show

22
9 9
Gabriel Iglesias is listed (or ranked) 22 on the list The Funniest Observational Comedians of All Time
Gabriel Iglesias Magic Mike, All That, Planes

23
9 9
Hannibal Buress is listed (or ranked) 23 on the list The Funniest Observational Comedians of All Time
Hannibal Buress The Eric Andre Show, Neighbors, Daddy's Home

24
2 2
Lewis Black is listed (or ranked) 24 on the list The Funniest Observational Comedians of All Time
Alexandre Lussier added Lewis Black The Daily Show, The Aristocrats, Lewis Black: Black on Broadway

25
5 6
David Brenner is listed (or ranked) 25 on the list The Funniest Observational Comedians of All Time
David Brenner Worth Winning, Snip

26
13 15
Woody Allen is listed (or ranked) 26 on the list The Funniest Observational Comedians of All Time
Woody Allen Annie Hall, Midnight in Paris, Vicky Cristina Barcelona

27
7 9
Ray Romano is listed (or ranked) 27 on the list The Funniest Observational Comedians of All Time
Ray Romano Everybody Loves Raymond, Ice Age, Ice Age: The Meltdown

28
6 8
Russell Peters is listed (or ranked) 28 on the list The Funniest Observational Comedians of All Time
Russell Peters Source Code, Russell Peters: The Green Card Tour - Live from The O2 Arena, A Russell Peters Christmas Special

29
4 7
Marc Maron is listed (or ranked) 29 on the list The Funniest Observational Comedians of All Time
Marc Maron Almost Famous, Sleepwalk with Me, Maron

30
3 7
Eddie Griffin is listed (or ranked) 30 on the list The Funniest Observational Comedians of All Time
Eddie Griffin Malcolm & Eddie, Undercover Brother, Deuce Bigalow: Male Gigolo

31
2 6
Paula Poundstone is listed (or ranked) 31 on the list The Funniest Observational Comedians of All Time
Paula Poundstone Home Movies, Science Court, When Stand Up Stood Out

32
7 12
Chris Tucker is listed (or ranked) 32 on the list The Funniest Observational Comedians of All Time
Chris Tucker Silver Linings Playbook, The Fifth Element, Rush Hour 2