Comedians

The Funniest Observational Comedians of All Time 

Ranker Comedy
Updated May 3, 2019 2.1k votes 380 voters 8.8k 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
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
Dave Chappelle is listed (or ranked) 2 on the list The Funniest Observational Comedians of All Time
Block Party, Half Baked, Chappelle's Show
3
Richard Pryor is listed (or ranked) 3 on the list The Funniest Observational Comedians of All Time
Richard Pryor: Live in Concert, Richard Pryor: Live on the Sunset Strip, Blazing Saddles
4
Bill Burr is listed (or ranked) 4 on the list The Funniest Observational Comedians of All Time
The Heat, Date Night, Walk of Shame
5
Chris Rock is listed (or ranked) 5 on the list The Funniest Observational Comedians of All Time
Chris Rock: Bigger & Blacker, Madagascar, Head of State
6
Jerry Seinfeld is listed (or ranked) 6 on the list The Funniest Observational Comedians of All Time
Seinfeld, Jerry Seinfeld: 'I'm Telling You for the Last Time', Comedian
7
Louis C.K. is listed (or ranked) 7 on the list The Funniest Observational Comedians of All Time
Late Night with Conan O'Brien, Louie, Louis C.K. Oh My God
8
Norm Macdonald is listed (or ranked) 8 on the list The Funniest Observational Comedians of All Time
Dirty Work, Billy Madison, Saturday Night Live
9
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
Jim Gaffigan is listed (or ranked) 10 on the list The Funniest Observational Comedians of All Time
It's Kind of a Funny Story, Away We Go, 17 Again
11
Ricky Gervais is listed (or ranked) 11 on the list The Funniest Observational Comedians of All Time
italosouza added
The Office, The Invention of Lying, Cemetery Junction
12
Larry David is listed (or ranked) 12 on the list The Funniest Observational Comedians of All Time
Seinfeld, Curb Your Enthusiasm, The Three Stooges
13
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
Don Rickles is listed (or ranked) 14 on the list The Funniest Observational Comedians of All Time
Toy Story, Toy Story 3, Toy Story 2
15
John Mulaney is listed (or ranked) 15 on the list The Funniest Observational Comedians of All Time
John Mulaney
Saturday Night Live, Mulaney
16
Brian Regan is listed (or ranked) 16 on the list The Funniest Observational Comedians of All Time
Brian Regan
Dr. Katz, Professional Therapist, Shorties Watchin' Shorties
17
Jim Jefferies is listed (or ranked) 17 on the list The Funniest Observational Comedians of All Time
Legit, Down and Dirty with Jim Norton, Jim Jefferies: I Swear to God
18
Ray Romano is listed (or ranked) 18 on the list The Funniest Observational Comedians of All Time
Everybody Loves Raymond, Ice Age, Ice Age: The Meltdown
19
Billy Connolly is listed (or ranked) 19 on the list The Funniest Observational Comedians of All Time
Brave, The Last Samurai, The Boondock Saints
20
Demetri Martin is listed (or ranked) 20 on the list The Funniest Observational Comedians of All Time
Late Night with Conan O'Brien, Demetri Martin. Person., Important Things with Demetri Martin
21
Anthony Jeselnik is listed (or ranked) 21 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
22
Gabriel Iglesias is listed (or ranked) 22 on the list The Funniest Observational Comedians of All Time
Magic Mike, All That, Planes
23
Lewis Black is listed (or ranked) 23 on the list The Funniest Observational Comedians of All Time
Alexandre Lussier added
The Daily Show, The Aristocrats, Lewis Black: Black on Broadway
24
Woody Allen is listed (or ranked) 24 on the list The Funniest Observational Comedians of All Time
Annie Hall, Midnight in Paris, Vicky Cristina Barcelona
25
Bill Hicks is listed (or ranked) 25 on the list The Funniest Observational Comedians of All Time
Comedy's Dirtiest Dozen, Bill Hicks: Sane Man, Bill Hicks Live: Satirist