The Top 25 Stand-Up Comedians of the 21st Century Up to Now (Nos. 25-16)

Breaking into stand-up comedy is never instantaneous. Before reaching fame, comedians face endless open-mic nights, long tours with minimal pay, and late-night performances for tough crowds. Climbing higher only increases the pressure to craft hour-long sets for tours, specials, and social media. Many also explore weekly podcasts as a form of digital improvisation.

As the first quarter of the 21st century concludes, Billboard has compiled a list of the top 25 stand-up comedians from the past 25 years. Experts who regularly work with comedians helped create the rankings, including festival directors, comedy club owners, and show bookers. The selection was limited to active stand-up performers, including international comics with a presence in the U.S.

The judges initially assembled a list of over 150 nominees, then each ranked their top 25. Voting was anonymous and weighted to determine the final list. The following are numbers 25 through 16.

25. Jon Stewart

Famed for hosting Comedy Central's The Daily Show from 1999 to 2015, Stewart began as a stand-up comedian. His routines blend political and cultural commentary with sharp humor. In 2024, he toured alongside Pete Davidson and John Mulaney. Aging and activism, particularly for veterans and first responders, feature prominently in his sets.

24. Billy Connolly

The Scottish comedian, nicknamed The Big Yin, retired from stand-up in the late 2010s but remains highly regarded. Known for his politically incorrect storytelling, Connolly's humor spans decades and includes both music and comedy. His routines, including pieces like Dwarf on a bus and Colonoscopy, are widely available online and continue to entertain new audiences.

23. Trevor Noah

Replacing Stewart on The Daily Show from 2015 to 2022, Noah uses his South African perspective to comment on American culture and race. In 2024, he ranked as the seventh highest-grossing comic, performing 94 shows for nearly 400,000 fans. His Netflix special Where Was I offers humorous critiques of American traditions and pop culture.

22. Jim Gaffigan

Gaffigan rose to prominence in the late 1990s, building a clean comedy brand focused on family life, eating habits, and self-deprecating humor. His 2024 Hulu special The Skinny highlighted his weight loss journey and playful reflections on public perception. Signature bits, like his Hot Pockets routine, showcase his comedic timing and relatability.

21. Gabriel Fluffy Iglesias

Iglesias started in the late 1990s under difficult circumstances, including financial struggles. He achieved a milestone in 2022 by selling out Dodger Stadium, documented in his Netflix special Stadium Fluffy. Iglesias comedy emphasizes storytelling, sound effects, and relatable commentary on race and culture, appealing to a wide audience.

20. Sarah Silverman

Silvermans deadpan humor allows her to address taboo subjects like gender, politics, and religion. Her career spans SNL, sitcoms, Disney films, and viral videos like Im Fking Matt Damon. In her 2025 Netflix special PostMortem, she transforms personal loss into sharp, provocative comedy while blending absurdity with insight.

19. Ali Wong

Wong is known for her candid, story-driven monologues on gender, race, and relationships. Her 2024 Netflix special Single Lady focuses on post-divorce life and sexuality. Her observational humor blends cultural critique with personal experience. She has earned awards for her performance in the dark comedy series Beef and is in a high-profile relationship with fellow comedian Bill Hader.

18. Patrice ONeal

ONeals comedy was fearless and brutally honest, tackling race, sex, and social hypocrisy. His raw style made him a comics comic, admired by peers like Bill Burr and Chris Rock. Despite passing away at 41 from complications related to diabetes, his influence remains significant, leaving a legacy of truth-driven, confrontational humor.

17. Wanda Sykes

Sykes began stand-up in the late 1980s and became a celebrated writer for The Chris Rock Show. Her comedy mixes sharp observation with wit, skewering societal norms, race, and pop culture. Specials like Im An Entertainer demonstrate her ability to combine conversational style with tightly crafted material, making her a standout comic voice.

16. Ricky Gervais

Creator of the Office franchise, Gervais is celebrated for his biting humor. His 2020 Golden Globes monologue epitomized his talent for satirical commentary, targeting Hollywood elitism, political correctness, and celebrity culture. Gervais work combines rapid-fire jokes with incisive social critique, cementing his reputation as a daring and influential comedian.

Author: Lucas Grant