What to watch
Best streaming guide in the US
On Thursday, May 14, 2026, Chris Rock shared a surprising piece of his romantic history during an appearance on the Fly On the Wall podcast with hosts David Spade and Dana Carvey.
While discussing his favorite hip-hop artists, Rock revealed a "lingering beef" with the late Tupac Shakur.
The comedian claimed that he and the legendary rapper often pursued the same women during the 1990s, noting that Tupac almost always won their attention.
The revelation has sparked significant conversation online, as fans quickly connected the dots to Rock’s complicated history with Jada Pinkett Smith.
Although Chris Rock did not name specific individuals on the podcast, many recall Pinkett Smith’s own admission in her 2023 memoir, Worthy, that Rock once asked her out when he believed she and Will Smith were headed for divorce.
Pinkett Smith has famously described Tupac as her "soulmate," further fueling the theory that this decades-old social circle contributed to the tension that culminated in the 2022 Oscars incident.
During the podcast, Rock explained that his exclusion of Tupac from his top rappers list stemmed from these personal frustrations rather than a lack of respect for the music.
He joked about the difficulty of competing for dates with a "revolutionary poet" and movie star, describing the era as a humbling time for his personal life.
The lighthearted conversation provided a rare look into the social dynamics of the 1990s entertainment scene, where comedians and rappers frequently moved in the same circles.
Chris Rock’s comments also touched on his wider dating history and his views on how the industry has changed.
He acknowledged that while he eventually found his own footing in the celebrity dating world, those early years of competing with figures like Tupac left a lasting impression.
Spade and Carvey laughed along with the story and noted that many entertainers from that era likely have similar tales of the Death Row Records star's magnetic presence out-shining them.
