2025 NAACP Image Awards: Dave Chappelle’s Funniest SNL Moments
At the 2025 NAACP Image Awards, the legendary Dave Chappelle will be honored with the prestigious President’s Award, recognizing his immeasurable contributions to comedy, culture, and social commentary. A master of his craft, Chappelle has spent decades pushing boundaries, blending sharp social critiques with razor-sharp comedic timing that has made him one of the most influential and polarizing figures in entertainment.
From his early stand-up days to revolutionizing Comedy Central with Chappelle’s Show, he has reshaped modern comedy while unapologetically speaking truth to power. With multiple Emmy Awards, a Mark Twain Prize for American Humor, and Grammy-winning stand-up specials, Chappelle’s legacy is cemented in entertainment history.
While his thought-provoking stand-up and legendary sketches are well-documented, Chappelle has also delivered some of the best SNL moments in recent memory, bringing his signature humor and insight to the iconic late-night stage. Today, we’re looking back at some of his best SNL moments, where he reminds us why he remains a true comedy giant.
Dave Chappelle’s Monologue – A Masterclass in Storytelling
Dave Chappelle takes the SNL stage with his signature cigarette in hand, commanding attention before he even utters a word. His monologues have become legendary for their ability to blend hilarity with hard truths, leaving audiences both laughing and deep in thought. Whether he’s tackling politics, race, or culture, Chappelle’s ability to deliver punchlines that pack a punch is unmatched.
Promo Power – The Calm Before the Storm
Even in SNL’s promos, Chappelle’s comedic energy is undeniable. His effortless charisma and deadpan delivery make every appearance feel like an event. As a host, he brings a level of unpredictability and genius that few can match, setting the tone for a night of laughs, edge, and brilliance.
Sketch Comedy Gold with Ego Nwodim
Here, Chappelle and Ego Nwodim create yet another unforgettable SNL moment, proving that his comedic chemistry is as sharp as ever. Whether he's playing an exaggerated character or reacting to the absurdity around him, Chappelle’s ability to command a scene makes every skit he’s in instant classic material.
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Reuniting with Donnell Rawlings – A Classic Duo
Few things in comedy are better than seeing Dave Chappelle and Donnell Rawlings together again. The longtime friends and collaborators bring back the chemistry that made Chappelle’s Show a cultural phenomenon, reminding us why their comedic partnership is one of the most beloved in modern comedy history.
Sharing His Star Power with Marcello Hernández and GloRilla
Chappelle’s presence on SNL elevates every moment, even alongside rising stars like Marcello Hernández and GloRilla. His ability to effortlessly adapt to any comedic scenario, whether he’s leading the joke or supporting it, proves why he’s in a league of his own.
Watch the 2025 NAACP Image Awards airing Saturday, February 22nd at 8 PM ET/ 8 PM PT on BET and CBS.
