The Best Stand-Up Comedy Specials of the 21st Century So Far Laughing Our Way Through the Years

The 21st century has been a wild ride so far, filled with ups and downs, twists and turns, and plenty of unexpected moments. But one thing that has remained constant is our need for laughter. In times of uncertainty and darkness, comedy serves as a beacon of light, bringing joy and relief to our lives. And in this digital age, we have been lucky enough to witness some of the best stand-up comedy specials ever created. From masterful storytelling to sharp social commentary, these specials have left us crying with laughter and begging for more. So let’s take a look at the best stand-up comedy specials of the 21st century so far.

1. Bo Burnham: “Make Happy”

Bo Burnham’s “Make Happy” is not just a stand-up special, it’s a masterpiece. The multi-talented comedian takes the audience on a rollercoaster ride of emotions, blending stand-up, music, and theatrics to create an unforgettable experience. From hilarious songs about the struggles of being a performer to poignant reflections on society and mental health, Burnham’s “Make Happy” is a tour de force. And with its clever use of visuals and satire, it’s a special that stays with you long after the final curtain call.

How to Use “Make Happy”

If you’re in need of a good laugh while also getting some thought-provoking insights, “Make Happy” is the perfect choice. Burnham’s razor-sharp wit and relatable humor make this special a must-watch for anyone looking to escape reality for a little while.

Examples from “Make Happy”

In “Make Happy,” Burnham tackles heavy topics like depression and existentialism, all while making the audience roar with laughter. One of the standout moments is his song “Kill Yourself,” which on the surface seems like a dark and twisted joke, but actually carries a powerful message about the pressure to be happy in today’s society.

Comparisons to Other Stand-Up Comedy Specials

“Make Happy” stands out from other stand-up comedy specials due to its unique blend of music, comedy, and social commentary. Burnham’s talent for mixing humor and poignancy makes this special a must-see for fans of stand-up comedy.

Advice for Watching “Make Happy”

Be prepared to have your emotions toyed with in the best way possible. “Make Happy” is not your typical stand-up special, so open your mind and let Bo Burnham take you on a journey.

2. Hannah Gadsby: “Nanette”

Hannah Gadsby’s “Nanette” is not just a comedy special; it’s a cultural phenomenon. In this raw and honest performance, Gadsby shares her experiences as a queer woman and challenges the traditional structure of stand-up comedy. With her sharp wit and unapologetic delivery, Gadsby takes on topics like homophobia, sexism, and trauma, all while making the audience laugh and cry at the same time.

How to Use “Nanette”

“Nanette” is a thought-provoking and emotionally charged special that will make you question the norms of society and the role comedy plays in it. It’s a must-watch for anyone looking for a unique and powerful stand-up experience.

Examples from “Nanette”

Gadsby’s story-telling abilities shine in “Nanette,” particularly in her stories about growing up gay in a small town and the struggles she faced as an LGBTQ+ person. But the most impactful moment comes when she reveals why she can’t continue doing the type of comedy she’s known for – because it perpetuates homophobia and allows for trauma to be dismissed as a joke.

Comparisons to Other Stand-Up Comedy Specials

“Nanette” blurs the lines between comedy and performance art, making it stand out from other stand-up specials. Gadsby’s unfiltered and honest approach sets it apart from traditional comedy shows, making it a must-see for anyone looking for something different.

Advice for Watching “Nanette”

Be prepared to have your perceptions challenged and your emotions stirred up. “Nanette” is not your usual feel-good comedy special, but it’s a powerful and important piece of storytelling that deserves to be seen.

3. Ali Wong: “Baby Cobra”

Ali Wong’s “Baby Cobra” is a no-holds-barred, hilarious take on pregnancy, marriage, and feminism. In this special, Wong fearlessly tackles taboo topics and shares her experiences as an Asian-American woman in the male-dominated world of comedy. With her quick wit and raunchy humor, she delivers one punchline after another, leaving the audience in stitches.

How to Use “Baby Cobra”

“Baby Cobra” is perfect for anyone who loves a good laugh and isn’t afraid of some edgy humor. Wong’s unapologetic delivery and relatable content make this special a crowd-pleaser that will have you quoting lines for days.

Examples from “Baby Cobra”

Wong’s tales of pregnancy and motherhood are both hilarious and brutally honest. She doesn’t shy away from sharing the less glamorous side of being pregnant, like dealing with hemorrhoids and breastfeeding struggles. But she also tackles more serious topics, such as the double standards faced by women and Asians in society.

Comparisons to Other Stand-Up Comedy Specials

Wong’s unapologetic and boundary-pushing style has drawn comparisons to comedy legends like Joan Rivers and Richard Pryor. “Baby Cobra” stands out for its ability to make audiences laugh while also challenging societal norms and stereotypes.

Advice for Watching “Baby Cobra”

Get ready to laugh until your cheeks hurt. Wong’s sharp humor and fearless delivery make “Baby Cobra” a must-see for anyone looking for a good time.

4. John Mulaney: “New in Town”

John Mulaney’s “New in Town” is a masterclass in storytelling and observational humor. In this special, Mulaney takes the audience on a journey through his life, from childhood memories to his struggles as a young adult. With his impeccable timing and charming persona, he has the audience hanging onto every word, laughing at every twist and turn.

How to Use “New in Town”

If you’re a fan of clever and relatable comedy, “New in Town” is a must-watch. Mulaney’s knack for turning everyday experiences into hilarious anecdotes makes this special a hit with audiences of all ages.

Examples from “New in Town”

One of the most memorable moments from “New in Town” is Mulaney’s story about a failed prank phone call as a child, which leads to him creating an entire fake persona that spirals out of control. His delivery and attention to detail make this bit a comedic masterpiece.

Comparisons to Other Stand-Up Comedy Specials

Mulaney’s clean and clever style of comedy sets him apart from other comedians in the industry. “New in Town” stands out for its ability to make audiences laugh without relying on shock value or offensive jokes.

Advice for Watching “New in Town”

Sit back, relax, and prepare to be entertained. “New in Town” is a feel-good special that will have you smiling from start to finish.

5. Dave Chappelle: “Sticks & Stones”

Dave Chappelle’s “Sticks & Stones” caused quite a stir upon its release, with some calling it offensive and others hailing it as a masterpiece. But love it or hate it, there’s no denying the impact this special had on the comedy world. Chappelle fearlessly tackles controversial topics like cancel culture and the LGBTQ+ community, all while making audiences laugh with his trademark wit and delivery.

How to Use “Sticks & Stones”

If you’re not easily offended and appreciate edgy and thought-provoking humor, “Sticks & Stones” is a must-watch. Chappelle’s ability to push boundaries and challenge societal norms makes this special a standout in the comedy landscape.

Examples from “Sticks & Stones”

Chappelle’s take on the Jussie Smollett scandal is one of the most talked-about moments from “Sticks & Stones.” With his sharp commentary and impeccable timing, he manages to make a serious and controversial topic hilarious.

Comparisons to Other Stand-Up Comedy Specials

Chappelle’s no-holds-barred approach has been compared to comedy legends like George Carlin and Richard Pryor. “Sticks & Stones” stands out for its ability to make audiences think while also delivering gut-busting laughter.

Advice for Watching “Sticks & Stones”

Buckle up and prepare for a wild ride. “Sticks & Stones” is not for the faint of heart, but if you’re open-minded and looking for some clever and provocative comedy, it’s a must-see.

6. Hannah Gadsby: “Douglas”

Hannah Gadsby’s second Netflix special, “Douglas,” continues her tradition of blending comedy and performance art. In this special, Gadsby explores topics such as autism, misogyny, and art history, using her signature blend of humor and honesty. With her quick wit and powerful storytelling, Gadsby takes the audience on a journey through her mind, leaving them laughing and reflecting on the world around them.

How to Use “Douglas”

“Douglas” is a must-watch for anyone who enjoyed “Nanette” and is looking for more of Gadsby’s thought-provoking and powerful brand of comedy. It’s also perfect for anyone who loves art history and wants to see it through a comedic lens.

Examples from “Douglas”

In “Douglas,” Gadsby uses her experience with autism to deliver poignant and humorous insights into how neurodiverse minds work. She also tackles heavy topics like misogyny and the lack of representation for marginalized groups in art history, all while making the audience laugh along the way.

Comparisons to Other Stand-Up Comedy Specials

“Douglas” follows in the footsteps of “Nanette” by blurring the lines between comedy and performance art. Gadsby’s unique blend of humor and vulnerability sets this special apart from traditional stand-up shows.

Advice for Watching “Douglas”

Get ready to have your mind blown and your funny bone tickled. “Douglas” is a special that will make you laugh, cry, and think all at once.


1. Are these specials appropriate for all ages?

While these specials are not necessarily inappropriate, they do contain mature themes and language, so parental discretion is advised.

2. Do I need to watch the previous specials of these comedians before watching these ones?

No, each of these specials can be enjoyed on its own without any prior knowledge of the comedian’s work.

3. Are there any other comedy specials from the 21st century that didn’t make the list?

Definitely! The 21st century has been full of amazing stand-up specials, so there are bound to be some great ones that didn’t make our list.

4. Can I watch these specials if I’m not a fan of stand-up comedy?

Absolutely! Each of these specials offers something unique and can be enjoyed by even those who don’t typically enjoy stand-up comedy.

5. Will there be more amazing stand-up comedy specials in the future?

With so many talented comedians out there, we have no doubt that the future holds even more amazing stand-up comedy specials.


The 21st century has been a golden era for stand-up comedy, with some of the most talented and fearless comedians taking the stage and making us laugh until our sides hurt. From addressing important social issues to sharing personal experiences and making us see the world in a whole new light, these specials have left a lasting impact on audiences around the world. So if you’re in need of a good laugh and some food for thought, look no further than the best stand-up comedy specials of the 21st century so far.

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