The last decade has been a transformative period in the world of stand-up comedy. From groundbreaking material that tackled social issues to performances that showcased deeply personal stories, the stand-up specials of the 2010s and 2020s have given audiences unforgettable laughs, insightful commentary, and new perspectives. Whether you’re a die-hard comedy fan or just looking for a great laugh, here’s a list of the funniest stand-up specials from the last decade that have defined modern comedy.
1. Dave Chappelle – Sticks & Stones (2019)
Platform: Netflix
Why It’s Iconic: Dave Chappelle has long been a master of blending humor with hard-hitting social commentary, and Sticks & Stones is no exception. With this special, Chappelle made waves for its unapologetic, boundary-pushing humor, touching on everything from cancel culture to celebrity scandals. Despite the controversy that followed, Sticks & Stones earned rave reviews for Chappelle’s unique ability to make difficult, often uncomfortable subjects feel funny while still challenging audiences to think.
Funniest Moment: Chappelle’s bit about the absurdity of “cancel culture” and his fearless approach to discussing the #MeToo movement drew both criticism and praise, but it’s one of the sharpest bits in modern comedy.
Why You Should Watch: It’s a no-holds-barred special that demonstrates Chappelle’s incredible ability to tackle controversial topics while keeping the audience laughing and thinking.
2. Hannah Gadsby – Nanette (2018)
Platform: Netflix
Why It’s Iconic: Nanette redefined what a comedy special could be. Hannah Gadsby’s hour-long performance took audiences on a rollercoaster ride of humor, vulnerability, and emotional catharsis. Gadsby challenged the traditional structure of stand-up comedy by blending personal trauma with sharp wit, creating a poignant piece that is both funny and deeply moving. Nanette won multiple awards and sparked global conversations about the role of comedy in storytelling and social change.
Funniest Moment: While the humor in Nanette is dark and deeply personal, Gadsby’s critique of traditional comedy and her ultimate declaration that she was quitting stand-up created a perfect, surreal mix of humor and heartbreak.
Why You Should Watch: Nanette is a powerful statement about the comedy industry, gender, and personal identity. It’s a must-watch for those who appreciate stand-up that goes beyond simple punchlines to make an impact.
3. John Mulaney – Kid Gorgeous (2018)
Platform: Netflix
Why It’s Iconic: John Mulaney’s Kid Gorgeous solidified him as one of the brightest stars in modern comedy. His clean, observational humor, combined with his impeccable storytelling, made this special a critical and commercial success. With Kid Gorgeous, Mulaney manages to blend personal anecdotes, sharp observations about society, and absurd stories with a level of charm that’s rare in the comedy world.
Funniest Moment: Mulaney’s riff on his experiences as a host of Saturday Night Live and his hilarious take on his childhood Catholic school experiences are crowd favorites. The bit about being mistaken for a “child genius” is a particular highlight.
Why You Should Watch: Kid Gorgeous is a masterclass in storytelling. Mulaney’s ability to make every joke feel like a carefully crafted narrative makes this one of the funniest and most intelligent specials of the decade.
4. Ali Wong – Baby Cobra (2016)
Platform: Netflix
Why It’s Iconic: Ali Wong’s Baby Cobra was a game-changer in many ways. As a pregnant woman performing her stand-up for a mostly male audience, Wong broke all the conventional rules of comedy. Her brutally honest and incredibly raunchy jokes about pregnancy, marriage, and gender roles had audiences rolling in the aisles. What made Baby Cobra stand out was Wong’s confidence and fearlessness in discussing topics that were rarely tackled with such rawness and humor.
Funniest Moment: Wong’s hilarious and unapologetic take on pregnancy—especially her vivid descriptions of her body’s changes—will leave you in stitches.
Why You Should Watch: Baby Cobra is a comedic triumph because of Wong’s authenticity and her willingness to talk about taboo topics with a sense of humor and strength that was completely new to stand-up.
5. Bo Burnham – Inside (2021)
Platform: Netflix
Why It’s Iconic: Bo Burnham’s Inside wasn’t just a comedy special—it was a musical, an art project, and a deep dive into the mental health struggles of living in isolation. Filmed entirely during the pandemic, Inside combined Burnham’s talent for dark, introspective comedy with social commentary, making it one of the most unique specials of the decade. It’s a brilliant exploration of loneliness, self-doubt, and the overwhelming nature of modern society—all wrapped in a series of catchy, satirical songs.
Funniest Moment: The song “Welcome to the Internet” is a clever and biting commentary on how technology shapes our lives in often absurd and dangerous ways.
Why You Should Watch: Inside isn’t just funny; it’s deeply emotional, existential, and thought-provoking. It’s perfect for anyone who appreciates dark humor, social commentary, and experimental comedy.
6. Chris D’Elia – No Pain (2020)
Platform: Netflix
Why It’s Iconic: Chris D’Elia’s No Pain was a hilarious exploration of the everyday absurdities that we all face. D’Elia’s signature style of energetic, sometimes chaotic storytelling makes this special stand out in a crowded field of stand-up performances. His comedic style may not be for everyone, but for those who love his rapid-fire delivery and observational humor, No Pain is a must-watch.
Funniest Moment: D’Elia’s take on his “biggest fear” and the way he plays with audience expectations through exaggerated, absurd scenarios had the crowd roaring.
Why You Should Watch: If you’re a fan of high-energy, fast-paced comedy that doesn’t take itself too seriously, No Pain delivers just the right amount of laughs and ridiculousness.
7. Ricky Gervais – Humanity (2018)
Platform: Netflix
Why It’s Iconic: Ricky Gervais’s Humanity was a bold return to the stage after a long hiatus from stand-up comedy. His take-no-prisoners attitude and dark, cutting humor shone through as he tackled everything from the absurdity of fame to the fragility of human existence. Gervais’s ability to blend his sharp wit with real-world commentary on human nature made Humanity a standout special.
Funniest Moment: Gervais’s bit about his “selfishness” and observations about modern celebrity culture are as brutal as they are hilarious.
Why You Should Watch: Humanity offers a rare, unfiltered look at Gervais’s comedic genius. His dry humor and fearless approach to touching on politically incorrect topics make this one of the best specials for fans of sharp, observational comedy.
8. Michelle Wolf – Nice Lady (2019)
Platform: Netflix
Why It’s Iconic: Michelle Wolf’s Nice Lady is a fearless exploration of feminism, society’s expectations of women, and the absurdity of modern life. Known for her acerbic wit and sharp social commentary, Wolf uses this special to tackle a wide range of topics—from her personal experiences to the broader societal issues that continue to affect women.
Funniest Moment: Her take on the gender pay gap and societal pressure to always “smile” is both hilarious and incredibly sharp.
Why You Should Watch: Nice Lady is a masterclass in mixing biting political humor with personal anecdotes. Michelle Wolf brings an energy and style to comedy that’s both fresh and necessary in today’s landscape.
9. Patton Oswalt – Annihilation (2017)
Platform: Netflix
Why It’s Iconic: Patton Oswalt’s Annihilation explores some deeply personal subjects with humor, particularly the grief and pain he experienced following the death of his wife. Oswalt blends dark humor with deep emotional honesty, making this one of the most poignant and funny specials of the decade.
Funniest Moment: Oswalt’s riff on how grief affects his day-to-day life—mixed with his brilliant observational humor—creates a perfect mix of sadness and humor.
Why You Should Watch: Annihilation is a stunning example of how comedy can be a vehicle for processing grief. It’s equal parts funny and cathartic, a perfect mix of humor and vulnerability.
10. Tiffany Haddish – Black Mitzvah (2019)
Platform: Netflix
Why It’s Iconic: Tiffany Haddish’s Black Mitzvah celebrates her success in comedy while also delving into her roots. Her exuberant, high-energy delivery and personal stories of struggle, triumph, and self-discovery make for an unforgettable hour of comedy.
Funniest Moment: Haddish’s hilarious recounting of her life in foster care and the way she embraced both her African-American and Jewish heritage is nothing short of inspiring.
Why You Should Watch: Black Mitzvah is a celebration of humor, perseverance, and the joy of being unapologetically yourself. Haddish brings a fresh, dynamic voice to the stand-up scene that is both inspiring and incredibly funny.
Conclusion
The last decade has produced some truly groundbreaking stand-up comedy specials. From poignant, emotional performances like Nanette to high-energy laugh riots like Sticks & Stones, these specials have shaped the comedy landscape in ways that will resonate for years to come. Whether you’re a fan of dark humor, personal stories, or boundary-pushing satire, these specials offer something for everyone—and are all essential viewing for anyone who appreciates the art of stand-up comedy.
