Comedy has evolved from small, dimly lit clubs to massive international stages, but it still relies on the basic formula of a comedian, a microphone, and a unique perspective. Over the years, comedians have influenced how we speak, challenged what’s legally acceptable, revolutionized television, and created a wealth of material – albums and performances – that continue to entertain audiences today.
This countdown highlights the most important moments in each comedian’s career – from their specials and tours to their most famous jokes and lasting impact on comedy. It showcases how they’ve achieved success, won awards, and ultimately helped shape stand-up comedy into what it is today.
20. Phyllis Diller
Phyllis Diller became famous in the late 1950s with her quick, energetic comedy and distinctive appearance. At a time when female comedians weren’t common, she performed in clubs, released comedy albums, appeared on popular TV variety shows, and toured theaters nationwide, attracting fans of all ages.
Her comedy routines were known for clever, well-crafted jokes and memorable characters, including running gags about her fictional husband, Fang. Beyond performing, she also wrote books and did voice work for cartoons. She continued to tour and perform live for many years, paving the way for other female comedians and proving to club owners that women could be successful headliners.
19. Bob Newhart
Bob Newhart’s first album, “The Button-Down Mind of Bob Newhart,” was a huge success in 1960, winning several awards – which was unusual for a comedy album back then. He became known for his funny phone conversations and his distinctive, hesitant way of speaking, all delivered with perfect comedic timing that translated well whether people were listening on records, watching on TV, or seeing him perform live.
He became famous for starring in popular TV shows like ‘The Bob Newhart Show’ and ‘Newhart’, all while continuing to perform stand-up comedy. He was known for his clever, well-crafted jokes that appealed to a wide audience, proving that subtle, observational humor could be just as successful as more boisterous styles.
18. Sam Kinison
Sam Kinison started his career as a preacher, and he brought that same passionate energy to his stand-up comedy. His performances were known for being loud and energetic, fitting well with the rock concert venues where he often performed. He became nationally known through appearances on HBO and late-night TV, which led to more and more club dates all over North America.
He made albums, performed live with a band, and even had his music videos played on TV. Sadly, his career ended abruptly in a car accident in 1992. However, his recordings and performances are still analyzed today for their rhythm, how he commanded the stage, and his clever use of quiet moments followed by bursts of sound.
17. Mitch Hedberg
Mitch Hedberg started with independently released albums, *Strategic Grill Locations* and *Mitch All Together*, which were full of quick, one-liner jokes. His performances on shows like ‘Comedy Central Presents’ and late-night television helped those albums gain a dedicated following, spreading popularity through recommendations from fans.
He designed sets that used repeating patterns, cleverly drew the eye away from flaws, and presented familiar things from surprising perspectives. Throughout the early 2000s, he toured with clubs and theaters, and after his death, previously unreleased recordings and designs showed how he perfected his style while performing live and working on television.
16. Norm Macdonald
Norm Macdonald was the host of Weekend Update on ‘Saturday Night Live’ in the mid-1990s, and he later went back to doing stand-up comedy, performing in theaters and clubs. His stand-up specials, like Me Doing Standup, were known for their long, rambling stories, drawn-out jokes, and unexpected punchlines that took their time to land.
I was such a fan of his! He was amazing at writing – his best-selling novel felt so personal, like a real memoir. And his talk shows weren’t just interviews; they always evolved into these hilarious, long-form bits. Then, in 2022, he released a special filmed at his home. It was different – just him performing new material without an audience, and it felt like a really intimate peek into his creative process and how he naturally spoke and wrote.
15. Billy Connolly
Billy Connolly became famous for his captivating storytelling, performing lengthy routines that combined songs, personal stories, and interactions with the audience. His popular television specials, ‘An Audience with Billy Connolly,’ were a hit in the UK and led to sold-out shows in large venues.
For many years, he traveled the world performing and created popular DVDs and books showcasing his work. Following a diagnosis of Parkinson’s disease, he stopped touring but continued to create art and write about his life. He left behind a vast collection of filmed performances for audiences to enjoy.
14. Don Rickles
As a huge fan of classic comedy, I always loved Don Rickles. He was a master of quick, playful insults – he started out working clubs, casinos, and theaters, and then became famous on shows like ‘The Tonight Show with Johnny Carson’ and ‘The Dean Martin Celebrity Roast’. He was a Vegas staple for decades, and people kept coming back to his shows just to be playfully roasted – it was all part of the fun!
Throughout his career in film and television, he continued to perform live shows well into his later years. A documentary and many late-night performances captured his impeccable comedic timing and ability to work any crowd – skills that continue to be studied by up-and-coming comedians.
13. Rodney Dangerfield
After a break from performing, Rodney Dangerfield returned to stand-up comedy in the 1960s and opened his own club, Dangerfield’s, in New York City in 1969. The club quickly became known for featuring up-and-coming comedians, many of whom gained national exposure through TV specials filmed there.
He achieved success with popular albums and sold-out shows, even appearing in films like ‘Caddyshack’ and ‘Back to School,’ all while continuing to perform stand-up comedy. His club became known for launching the careers of many famous comedians, and his TV specials helped introduce fresh comedic talent to audiences nationwide.
12. Steve Martin
Steve Martin became hugely popular in the 1970s with his comedy albums, “Let’s Get Small” and “A Wild and Crazy Guy.” He quickly followed this up with sold-out national tours where he combined clever jokes, slapstick comedy, magic tricks, and playing the banjo – creating a high-energy, variety-show-style performance.
After taking a break from stand-up comedy in the early 1980s, he eventually returned to the stage, touring with Martin Short. Their partnership was featured in the Netflix special ‘An Evening You Will Forget for the Rest of Your Life,’ and he continued to pursue both music and writing.
11. Louis C.K.
As a comedy fan, I remember when Louis C.K. totally shook things up back in 2011. He put his ‘Live at the Beacon Theater’ special up for sale *directly* on his website, and it was surprisingly affordable – a flat price, no messing around. A lot of other comedians started doing the same thing after that. He kept the momentum going with yearly specials, constantly working out new material at clubs, and big tours that helped him refine everything quickly. It was a really smart way to build an audience and stay fresh.
Louis C.K. is known for creating the shows ‘Louie’ and ‘Horace and Pete,’ both of which uniquely combined stand-up comedy with traditional storytelling. He’s won awards for his comedy specials, and continues to release new material through his own platform.
10. Jerry Seinfeld
Jerry Seinfeld became a major figure in comedy by starting with stand-up performances in clubs, which eventually led to his own TV show, ‘Seinfeld’. After performing his classic routines for years, he created a new comedy special, ‘I’m Telling You for the Last Time’, and continues to develop fresh material for both live shows and streaming services.
Jerry Seinfeld became known for ‘Comedians in Cars Getting Coffee,’ a show where he’d have casual conversations with other comedians, mixed with short stand-up performances and glimpses of them at comedy clubs. His later Netflix specials, like ‘Jerry Before Seinfeld’ and ‘23 Hours to Kill,’ featured old notebooks, new material, and maintained the same straightforward, effective style he uses on stage.
9. Chris Rock
Chris Rock became a star with his 1996 comedy special, ‘Bring the Pain,’ which won awards and allowed him to perform in much larger venues. He continued his success with subsequent specials like ‘Bigger and Blacker’ and ‘Never Scared,’ consistently touring both domestically and internationally and getting frequent airplay on cable television.
He’s a successful performer who has hosted the Oscars, written popular books, and consistently released highly-anticipated comedy specials like ‘Tamborine’ and ‘Selective Outrage’. His live shows are still large-scale events, developed and refined through extensive practice in smaller clubs before moving to theaters and streaming platforms.
8. Robin Williams
Robin Williams first gained acclaim for his improvisational stand-up in the mid-1980s with the highly regarded ‘A Night at the Met’ recording, which showcased his energetic style and diverse characters. After focusing on film for a while, he returned to stand-up with ‘Weapons of Self Destruction,’ a successful arena tour that was later broadcast as an HBO special.
He never stopped doing stand-up, even with his television and film work. He consistently returned to clubs in San Francisco and Los Angeles to test out new material. Recordings of his performances, benefit shows, and tours demonstrate how he refined his comedy in front of audiences.
7. Bill Hicks
Bill Hicks spent years performing stand-up, starting as a teenager, before filming his comedy specials ‘Relentless’ and ‘Revelations’ in the early 1990s. He also released albums like Arizona Bay and often explored similar themes across his different performances.
A performance recorded in 1993 for a late-night show was originally edited down, but later broadcast in its entirety after his passing, becoming part of his lasting artistic legacy. Additionally, released albums and films compiled previously unreleased recordings and rare materials, offering valuable insight into his creative process and how his most famous routines developed.
6. Joan Rivers
Joan Rivers was a popular regular and fill-in host on ‘The Tonight Show with Johnny Carson.’ In 1986, she made history as the first woman to host a network late-night show with ‘The Late Show Starring Joan Rivers.’ She then found success with ‘The Joan Rivers Show,’ a daytime program that earned numerous awards, all while continuing to perform stand-up.
Her comedy shows weren’t just performances – she constantly updated them with new material from her albums, concert movies, and stage productions to keep them fresh. Beyond that, she became a well-known media personality through appearances on red carpets and her role on ‘Fashion Police,’ all while consistently touring and performing live on stage.
5. Eddie Murphy
Eddie Murphy quickly became a huge star, releasing his groundbreaking stand-up films, ‘Delirious’ and ‘Raw’, before he even turned thirty. He started on ‘Saturday Night Live’ at just nineteen years old and played a key role in bringing the show back to popularity. His memorable characters and comedy routines on ‘SNL’ directly boosted ticket sales for his stand-up tours, helping him move from clubs to large arenas.
He became a famous movie star, appearing in many successful films that kept him well-known worldwide, and he took a break from stand-up comedy for a long time. He eventually returned to the stage, hosting ‘Saturday Night Live,’ and has hinted at new stand-up plans. His older comedy specials and recordings are still popular with fans and continue to be studied by aspiring comedians.
4. Dave Chappelle
Dave Chappelle created ‘Chappelle’s Show’ and used the show’s popularity to perform stand-up extensively before unexpectedly pausing his career at its peak. He later revitalized his stand-up routine with frequent, lengthy club performances, surprise appearances, and extended theater engagements, quickly amassing a large number of performance hours.
Since 2017, he’s released several comedy specials on Netflix, including ‘The Age of Spin’, ‘Deep in the Heart of Texas’, ‘Equanimity’, ‘The Bird Revelation’, ‘Sticks and Stones’, and ‘The Closer’. He was also awarded the Mark Twain Prize for American Humor and still performs new material at large shows in arenas and outdoors.
3. Lenny Bruce
Lenny Bruce’s comedy albums, like ‘The Sick Humor of Lenny Bruce,’ made him a key player in the fight for free speech, changing the boundaries of what comedians could discuss onstage. His arrests and trials in the early 1960s highlighted the legal challenges facing performers and the limits placed on language used in public venues.
In 2003, a comedian received a posthumous pardon for an obscenity conviction from 1964, bringing attention to the significance of his legal battles. Today, his performances – both live and recorded – are still widely used by comedians and researchers studying the history of free speech in stand-up comedy.
2. George Carlin
George Carlin’s many HBO comedy specials documented shifts in language, politics, and daily life over a period of more than thirty years, essentially creating a video history of the era. He became famous for his routine listing seven forbidden words, which even led to a Supreme Court case about what could be said on television and what was considered indecent.
He was a hugely successful author and continued performing live well into his later years, frequently recording a special and immediately starting to prepare new material. His work, both written and performed on stage, earned him numerous Grammy Awards and the prestigious Mark Twain Prize.
1. Richard Pryor
Let me tell you, Richard Pryor wasn’t just a comedian, he was a phenomenon. His concert films and albums – things like ‘Richard Pryor Live in Concert’ and ‘Live on the Sunset Strip’ – absolutely *blew up*, selling like crazy and getting replayed constantly. He racked up a ton of Grammy Awards for his comedy recordings, and before he even hit the big screen, he was writing for TV. But even after making movies, he *never* stopped doing stand-up, which is a testament to his dedication and, frankly, how amazing he was.
He performed in major venues, created iconic comedy specials, and shaped the sound of comedy clubs for years through his recordings. His work with fellow artists, combined with extensive touring both in the US and internationally, resulted in a collection of material that continues to be incredibly important to the history of stand-up comedy.
If you have other suggestions for this list, let us know in the comments! Tell us who you’d like to add or replace.
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2025-09-21 22:02