Chelsea Handler roasts ‘Favorite Ex’ 50 Cent with hilarious dig at Critics Choice Awards

Chelsea Handler roasts 50 Cent during the 2026 Critics’ Choice Awards, bringing her signature sharp humor to the stage. Her monologue was packed with clever jabs at celebrities and Hollywood heavyweights alike. Among the standout moments were her playful digs at rapper Curtis “50 Cent” Jackson, who happens to be her former partner, and rapper Nicki Minaj. Handler’s comedic timing and candid commentary once again reminded the audience why she remains one of Hollywood’s most fearless hosts.

Handler’s monologue blended nostalgia and wit as she touched on past relationships and current pop culture controversies. The comedian has a history of humorously reflecting on her romantic life, and this year’s awards show was no exception. Handler made it clear that no one, celebrity or otherwise, was safe from her tongue-in-cheek commentary.

Beyond the personal jokes, Handler also demonstrated her ability to tackle broader cultural topics with levity. Whether referencing Hollywood power struggles or rap industry feuds, her monologue kept the audience engaged while mixing insight with humor.

Chelsea Handler roasts 50 Cent with a clever reference to Netflix rivalry

Chelsea Handler roasts 50 Cent during the awards show, drawing laughter with a joke about his ongoing rap-world rivalry with Sean “Diddy” Combs. The two dated briefly in the early 2010s after Jackson appeared on her E! talk show, wooing Handler with flowers. Handler has affectionately called him her “favorite ex,” during an appearance on Hous Guest, but that didn’t prevent her from poking fun at him while discussing his Netflix series Sean Combs: The Reckoning.

Handler quipped, “The cast of KPop Demon Hunters is here, not to be confused with Netflix’s other music movie, 50 Cent: Diddy Hunter.” The line landed perfectly, blending Handler’s personal connection with 50 Cent and a playful commentary on the rapper’s public persona.

Handler’s monologue emphasized that the jokes were lighthearted and affectionate. While she referenced her romantic past with Jackson, it was clear the humor was rooted in admiration and respect rather than malice.

Chelsea Handler roasts Nicki Minaj with bold humor

Handler didn’t stop at 50 Cent; she also turned her attention to Nicki Minaj, delivering a sharp-witted commentary on the rapper’s recent controversies. While discussing the hit vampire film Sinners, Handler remarked, “Sinners was a massive blockbuster! Although, I haven’t been invited into a Black person’s house since, except Nicki Minaj’s, but who wants to go over there?”

The joke came amid backlash surrounding Minaj’s recent appearance at a Turning Point USA event, where she discussed politics and faith alongside Erika Kirk and made statements about former President Donald Trump. Handler’s playful dig acknowledged the ongoing public debate surrounding Minaj, while keeping the tone humorous.

Handler’s comedic approach highlights how celebrity culture intersects with social commentary. Her remarks on Minaj demonstrate her ability to address sensitive topics with levity, using wit as a lens to examine public perception. A petition calling for Minaj to be deported to her native Trinidad and Tobago has also recently surpassed 100,000 signatures, adding context to Handler’s joke.

A blend of humor, insight, and celebrity culture

Chelsea Handler Roasts not only deliver laughs but also offer insight into Hollywood relationships and the rap industry. Her references to past partners like 50 Cent, and contemporary figures like Nicki Minaj, showcase her unique ability to blend personal experiences with industry commentary. Handler’s jokes reflect her deep familiarity with pop culture and her comfort navigating controversial topics while remaining engaging.

Her monologue at the Critics Choice Awards also served as a subtle commentary on celebrity rivalries and alliances. The combination of humor, timing, and cultural awareness made her segments about 50 Cent and Nicki Minaj memorable highlights of the evening.

Handler’s approach to comedy underscores a larger trend in award shows: audiences enjoy humor that is personal, yet relevant to broader industry narratives. Chelsea Handler Roasts moments demonstrate how clever wordplay, affectionate jabs, and cultural commentary can coexist, keeping viewers entertained while sparking conversation.

By mixing affectionate commentary on past relationships with current controversies in rap and pop culture, Handler created a monologue that balanced humor, nostalgia, and commentary. Her jokes about 50 Cent and Nicki Minaj reinforced her reputation as a host unafraid to tackle sensitive subjects with sharp wit and intelligence.