Bad Bunny Turns Late Night Upside Down as Stephen Colbert Joins His Unforgettable Bilingual Block Party

On a humid July evening in 2025, The Late Show with Stephen Colbert transformed into something extraordinary — a vibrant cultural crossover that instantly became one of the most talked-about moments in late-night history. When Stephen Colbert, the king of satire, met Bad Bunny, the global reggaeton superstar, the result was an electrifying fusion of humor, music, and heartfelt authenticity that left audiences and industry insiders alike buzzing.

With CBS announcing that The Late Show would end its run in May 2026, the show’s final season was already under the spotlight. Officially, the cancellation was framed as a budgetary decision amid a shifting media landscape, but rumors hinted at creative tensions between Colbert’s sharp political edge and cautious network executives.

Unfazed, Colbert opened the episode with a bold promise:
“Now the gloves are off, and possibly the bow tie too. We’re going big.”

Enter Bad Bunny — or Benito Antonio Martínez Ocasio — fresh from a record-breaking 31-show residency in San Juan that energized Puerto Rico’s economy and culture. His visit to New York included back-to-back late-night appearances, but it was his stop on Colbert’s stage that would become legendary.

From their first exchange, the energy was palpable. Colbert, in a tailored navy suit and signature glasses, greeted Bad Bunny by his given name, “Benito,” setting a tone of playful familiarity.

“Benito,” Colbert teased, “you’ve performed for hundreds of thousands, broken every record, and made Rolling Stone covers look like fashion week. What’s left for you to conquer?”

Bad Bunny, sporting a colorful golfer’s outfit — a nod to his upcoming cameo in Happy Gilmore 2 — smiled and replied in a smooth mix of English and Spanish:
“Maybe teach you to dance, Stephen.”

Laughter and cheers erupted as the two effortlessly bounced between comedy and cultural connection, trading jokes about mullets, fashion, and dance moves.

Midway through the show, Bad Bunny declared,
“We make-over you. Right now.”

What followed was pure late-night magic. The studio transformed into a playful salon: a mullet wig, electric blue nail polish, and a flowing Puerto Rican-print scarf appeared. Colbert gamely submitted to the makeover, donning the wig and letting Bunny paint his thumbnail blue.

As the band launched into a reggaeton remix of “Tití Me Preguntó,” Bunny demonstrated the signature hip sway. To everyone’s surprise, Colbert nailed the moves with flair.

“If this is the end of my show,” Colbert quipped mid-dance, “I’m at least going out dancing!”

The audience roared, and clips of the moment quickly went viral, racking up millions of views across platforms. Even rival late-night hosts admitted it was some of the funniest TV they’d seen in years.

The segment wasn’t just about fun. Colbert and Bad Bunny delved into identity, duality, and authenticity. Colbert asked how Bunny balances his two personas: the energetic Bad Bunny and the quieter Benito.

Bunny reflected,
“Bad Bunny is energy — the stage, the crowd, the music. Benito is the quiet one who calls his mom every Sunday and eats mofongo with friends.”

Colbert smiled knowingly, comparing it to his own experience balancing his public and private selves.

The conversation also touched on Bunny’s San Juan residency, which featured surprise guests like Ricky Martin and Daddy Yankee. For Bunny, the shows were about more than entertainment — they were a celebration of Puerto Rico’s resilience.

Bad Bunny’s commitment to singing exclusively in Spanish is a deliberate statement of cultural pride. “Why change for applause?” he said. “Spanish is home. Music has no borders.”

Colbert praised Bunny’s impact, noting,
“And yet somehow, you’ve turned half of America into bilingual dancers.”

The episode also teased Bunny’s role in Happy Gilmore 2 , where he plays Adam Sandler’s caddy. Bunny shared behind-the-scenes stories about the improvisational chaos on set and their decision to make the film Spanglish, much to the delight of fans.

With the show’s end looming, this episode felt like a celebration of everything Colbert has stood for: sharp intellect, inclusivity, and the courage to be authentic and a little weird.

When Bunny presented Colbert with custom Adidas sneakers inscribed “Abuelo Perrea” (“Grandpa Dances”), the audience erupted. Colbert joked,
“These will replace my dress shoes at the Emmys.”

The next day, The Late Show experienced a 20% ratings boost among younger viewers. Clips of the makeover and dance dominated morning shows and social media. Critics called it “a bilingual balm for turbulent times,” and The Hollywood Reporter dubbed it “a farewell season gem.”

CBS insiders quietly wondered if the cancellation had been premature, recognizing that moments like this keep audiences engaged.

The magic of the Colbert-Bunny collaboration lay in its authenticity. No forced sketches, no overproduced bits — just two artists being unapologetically themselves. Both use humor and music to speak truth and navigate public expectations while staying true to their identities.

Colbert summed it up perfectly:
“Comedy and music aren’t about escape. They’re about survival. You make us dance through the storm.”

Bunny responded with a smile:
“And you make us laugh in the rain.”

As The Late Show approaches its final curtain, episodes like this remind viewers why Stephen Colbert became a late-night giant. He didn’t just host interviews; he created spaces for genuine connection and cultural conversation.

Bad Bunny’s visit may not have been the finale, but it will be remembered as the moment late-night felt new again — alive, bilingual, joyful, and unstoppable.

As the credits rolled, Bunny hugged Colbert and whispered something inaudible. Colbert turned to the camera with a grin:
“Benito says I still can’t dance. But he’s wrong — I just need more practice.”

The band played out with a Latin beat, and for a moment, late-night television felt reborn.