Issa Rae is taking another swing at HBO comedy, this time stepping into the world of professional boxing and male friendship. The latest project adds another chapter to a television run that has repeatedly made room for Black characters whose lives are allowed to be funny, messy, ambitious and specific. The best Issa Rae shows have rarely felt interested in explaining Black life to outsiders. Instead, they have built entire worlds around the people already living it.
According to Variety, HBO has ordered a pilot currently known as “Untitled Male Friendship Show,” written and executive produced by Rae. The comedy follows Menzel, a 30-year-old barber and aspiring sports manager whose best friend, JB, is an emerging professional boxer in Las Vegas. The network’s description says the men will “navigate ambition, insecurity, loneliness and the double-edged sword of success within the high-stakes world of professional boxing in Las Vegas.” Importantly, HBO has ordered a pilot at this stage, not a full series.
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The project also reconnects Rae with one of the key architects of “Insecure.” Variety’s report says Prentice Penny will serve as showrunner and executive producer and direct the pilot after serving as showrunner across all five seasons of “Insecure.” Jax Clark will executive produce through Rae’s HOORAE banner, while Jonathan Berry and Dave Becky are also executive producers. That reunion matters because the new comedy appears ready to revisit one of Rae’s strongest creative lanes, friendship under pressure, while shifting the perspective toward Black men, sports, and the business surrounding boxing.
The foundation for all of this remains “Insecure.” According to HBO, Rae and Larry Wilmore created the series, with Rae starring as Issa Dee while also executive producing. The show ran for five seasons before concluding in 2021, following Issa and the people closest to her through changing friendships, romantic relationships, and careers. HBO also confirmed that Yvonne Orji, Jay Ellis, Natasha Rothwell and other core cast members helped build the ensemble around Rae. Of all the Issa Rae shows, “Insecure” established the blueprint: culturally specific storytelling without sacrificing awkwardness, flaws or everyday humor.
While “Insecure” was still on the air, Rae widened her producing footprint with “A Black Lady Sketch Show.” According to HBO’s production credits, Robin Thede created, wrote, executive produced, and starred in the sketch comedy, while Rae executive produced through HOORAE. The series centered Black women inside absurd, relatable, and often surreal comedy worlds and ultimately ran for four seasons. HBO’s press materials also confirm the show earned multiple Emmy Awards during its run. The series gave performers including Thede, Gabrielle Dennis, Ashley Nicole Black and Skye Townsend space to jump between characters and genres without narrowing Black women into one comedic archetype.
Rae then turned the lens toward reality television with “Sweet Life: Los Angeles.” HBO Max described the unscripted series as a look at young Black Angelenos pursuing love, careers, friendship and adulthood in South Los Angeles. Rae served as an executive producer, and the series debuted in 2021 before returning for a second season in 2022. Rae said at the time, “We’re so proud to present a grounded and fun slice of young Black LA life.” The series was later canceled after two seasons, according to Entertainment Weekly, but its focus fit naturally beside other Issa Rae shows by keeping South Los Angeles and young Black ambition at the center.
“Rap Sh!t” moved that ambition into the music business. According to Warner Bros. Discovery’s official series materials, the comedy followed Shawna, played by Aida Osman, and Mia, played by KaMillion, estranged high school friends who reunite in Miami to form a rap group. Rae executive produced, wrote the premiere, and worked alongside showrunner Syreeta Singleton. Yung Miami and JT of City Girls served as co-executive producers, while Raedio handled music supervision. The show ran for two seasons before Max declined to move forward with a third, according to TVLine. Even with its short run, “Rap Sh!t” pushed Rae’s television world into social media performance, female rap, and the compromises surrounding entertainment industry success.
Then came “Project Greenlight,” where Rae shifted some of the attention behind the camera. According to Max’s official press materials, the 2023 revival focused on emerging women filmmakers and followed director Meko Winbush as she made her first feature, “Gray Matter.” Rae executive produced and appeared as a mentor alongside Gina Prince-Bythewood and Kumail Nanjiani. The ten-episode docuseries made the filmmaking process itself the story, adding another dimension to the larger pattern across Issa Rae shows: building platforms where new voices can actually make the work, not simply talk about needing more representation.
That is what makes the new HBO pilot feel bigger than a simple return to familiar territory. Rae has moved from the friendship politics of “Insecure” to Black women driving sketch comedy, young Black Los Angeles navigating reality television, women rappers chasing success, and filmmakers fighting to get their first shot. Now, according to Variety, she and Penny are putting Black male friendship inside the pressure cooker of professional boxing. There is no guarantee the pilot becomes a series, but Rae’s television history shows a creative appetite that keeps expanding rather than repeating itself. For audiences who have watched that evolution since Issa Dee first started talking herself through life in the mirror, the culture is still getting new heat.
