Conan O’Brien, known for his sharp wit and comedic daring, set Hollywood abuzz when he unexpectedly reignited the highly publicized conflict between rap superstars Kendrick Lamar and Drake at the 97th Academy Awards, generating gasps, laughter, and controversy that extended well beyond the Dolby Theatre.

Hosting the prestigious ceremony on March 2, 2025, the 61-year-old veteran comedian and beloved late-night icon surprised audiences midway through the night with a provocative jab referencing the intense legal battles and heated lyrical exchanges between two of music’s most influential figures.

As the Oscars progressed smoothly through its glamorous evening, O’Brien paused, delivering with a mischievous grin the now-infamous remark: “We’re halfway through the show, which means it’s time for Kendrick Lamar to come out and call Drake a pedophile.”

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This sharp comedic reference immediately triggered audible reactions, mixing laughter and gasps, as O’Brien quickly followed up with a playful reassurance, “Don’t worry, I’m lawyered up,” acknowledging the very real lawsuits Drake recently brought against both Universal Music Group and iHeartMedia concerning Lamar’s provocative hit song “Not Like Us.”

This unexpected Oscars moment reopened conversations about the complicated feud that has rocked the music industry since Lamar’s Grammy-winning track explicitly targeted Drake with deeply personal accusations and aggressive lyrical confrontations.

“Not Like Us,” recognized as one of Kendrick Lamar’s most critically-acclaimed songs, had swept five Grammy awards earlier in 2025, amplifying its controversial impact and setting off intense public discussions about artistic expression and personal boundaries in the rap community.

The feud originally intensified in late 2024, when Drake accused Universal Music Group, the company managing both artists, of intentionally promoting and amplifying Lamar’s track despite its highly contentious lyrics.

According to legal documents from late November 2024, Drake accused Universal Music of orchestrating a deliberate marketing campaign designed to saturate streaming platforms and radio waves, ultimately causing significant personal harm and reputational damage.

Drake’s legal filings claimed that “Not Like Us” contained false and damaging allegations, intended explicitly to provoke and harm him publicly.

The artist went further, asserting in his lawsuits that UMG’s actions were not merely commercial promotions but calculated efforts to create viral controversy at his expense, a claim that was vehemently denied by Universal Music Group.

In a strongly-worded public statement, the music giant argued that Drake’s allegations were not only untrue but also “illogical,” given the extensive financial investments and successful partnership between the artist and label over the years.

The tension reached a temporary resolution only days before the Oscars, with Drake reaching a settlement with iHeartMedia—though notably, his lawsuit against Universal Music Group remains unresolved.

This fresh legal update lent additional weight to O’Brien’s remark, making it particularly provocative in a room filled with influential entertainment industry leaders closely following the unfolding drama.

Public reaction to Conan’s joke quickly flooded social media, dividing opinions sharply.

While some praised O’Brien for bravely addressing current pop-culture tensions with his trademark irreverence, others criticized the move as insensitive given the seriousness of the allegations involved.

Nonetheless, Conan’s reputation as a host who pushes comedic boundaries remained intact, reinforcing his status as one of Hollywood’s most unpredictable and fearless personalities.

Meanwhile, Kendrick Lamar and Drake, both notably absent from the Oscars ceremony, remained silent in the immediate aftermath, leaving fans and industry insiders speculating on their potential responses.

Observers noted that Lamar has historically maintained a policy of letting his music speak for itself, rarely engaging publicly with criticisms or jokes aimed his way.

Drake, on the other hand, has a track record of responding directly to public provocations, often through strategic releases or pointed social media statements.

O’Brien’s audacious joke comes amidst broader public scrutiny over celebrity feuds and the thin line between entertainment and personal offense.

Industry experts speculate this renewed attention could further fuel the longstanding rivalry, potentially leading to new music or further legal battles as both rappers grapple with public perception and the professional implications of their intense conflict.

In addition to stirring controversy, Conan O’Brien’s jab also highlighted an ongoing shift in the Oscars’ cultural relevance.

Once an event strictly focused on cinema, the ceremony now routinely incorporates broader pop-culture references, reflecting a changing media landscape where music, celebrity culture, and public controversy increasingly intersect with Hollywood traditions.

The evening continued after O’Brien’s joke with notable tension lingering in the air, though the comedian smoothly transitioned into less contentious territory, carefully navigating away from any further escalation.

Still, the remark firmly planted itself as one of the evening’s defining moments, dominating post-Oscars headlines and sparking lively debates about comedic boundaries, artistic freedom, and the responsibilities inherent in hosting such high-profile events.

As Hollywood reflects on another memorable Oscars night, Conan O’Brien’s daring commentary reminds everyone of comedy’s potent role in public discourse—whether provocative, hilarious, or deeply uncomfortable—and ensures that the drama surrounding Kendrick Lamar and Drake will continue to captivate audiences well beyond Oscar season.