Comedians The Funniest Observational Comedians of All Time  

Ranker Comedy
1.2k votes 242 voters 5k views 34 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
63 34
Jerry Seinfeld is listed (or ranked) 1 on the list The Funniest Observational Comedians of All Time
Seinfeld, Jerry Seinfeld: 'I'm Telling You for the Last Time', Comedian
2
54 27
George Carlin is listed (or ranked) 2 on the list The Funniest Observational Comedians of All Time
Dogma, Cars, Bill & Ted's Excellent Adventure
3
48 24
Bill Burr is listed (or ranked) 3 on the list The Funniest Observational Comedians of All Time
The Heat, Date Night, Walk of Shame
4
44 23
Dave Chappelle is listed (or ranked) 4 on the list The Funniest Observational Comedians of All Time
Block Party, Half Baked, Chappelle's Show
5
56 36
Louis C.K. is listed (or ranked) 5 on the list The Funniest Observational Comedians of All Time
Late Night with Conan O'Brien, Louie, Louis C.K. Oh My God
6
28 14
Richard Pryor is listed (or ranked) 6 on the list The Funniest Observational Comedians of All Time
Richard Pryor: Live in Concert, Richard Pryor: Live on the Sunset Strip, Blazing Saddles
7
36 22
Chris Rock is listed (or ranked) 7 on the list The Funniest Observational Comedians of All Time
Chris Rock: Bigger & Blacker, Madagascar, Head of State
8
35 22
Larry David is listed (or ranked) 8 on the list The Funniest Observational Comedians of All Time
Seinfeld, Curb Your Enthusiasm, The Three Stooges
9
28 16
Mitch Hedberg is listed (or ranked) 9 on the list The Funniest Observational Comedians of All Time
Almost Famous, Lords of Dogtown, Los Enchiladas!
10
30 20
John Mulaney is listed (or ranked) 10 on the list The Funniest Observational Comedians of All Time
Saturday Night Live, Mulaney
11
28 20
Jim Gaffigan is listed (or ranked) 11 on the list The Funniest Observational Comedians of All Time
It's Kind of a Funny Story, Away We Go, 17 Again
12
18 11
Don Rickles is listed (or ranked) 12 on the list The Funniest Observational Comedians of All Time
Toy Story, Toy Story 3, Toy Story 2
13
27 20
Eddie Murphy is listed (or ranked) 13 on the list The Funniest Observational Comedians of All Time
Beverly Hills Cop, Trading Places, Coming to America
14
18 12
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
22 18
Jim Jefferies is listed (or ranked) 15 on the list The Funniest Observational Comedians of All Time
Legit, Down and Dirty with Jim Norton, Jim Jefferies: I Swear to God
16
18 14
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
14 11
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
7 4
Ricky Gervais is listed (or ranked) 18 on the list The Funniest Observational Comedians of All Time
italosouza added The Office, The Invention of Lying, Cemetery Junction
19
4 1
Anthony Jeselnik is listed (or ranked) 19 on the list The Funniest Observational Comedians of All Time
homedecorbylauren added Miss March, Down and Dirty with Jim Norton, Down & Dirty with Jim Norton
20
15 13
Gabriel Iglesias is listed (or ranked) 20 on the list The Funniest Observational Comedians of All Time
Magic Mike, All That, Planes
21
19 19
Woody Allen is listed (or ranked) 21 on the list The Funniest Observational Comedians of All Time
Annie Hall, Midnight in Paris, Vicky Cristina Barcelona
22
18 18
Bill Hicks is listed (or ranked) 22 on the list The Funniest Observational Comedians of All Time
Comedy's Dirtiest Dozen, Bill Hicks: Sane Man, Bill Hicks Live: Satirist
23
13 13
Billy Connolly is listed (or ranked) 23 on the list The Funniest Observational Comedians of All Time
Brave, The Last Samurai, The Boondock Saints
24
8 9
David Brenner is listed (or ranked) 24 on the list The Funniest Observational Comedians of All Time
Worth Winning, Snip
25
7 8
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