Issa Rae Is Heading Back to HBO, and She’s Bringing an Insecure Favorite With Her

Issa Rae and HBO are apparently not done with each other just yet. Nearly five years after Insecure wrapped its acclaimed run, Rae is heading back to familiar territory with a new half hour comedy pilot that trades awkward Los Angeles dating adventures for friendship, ambition and the professional boxing world of Las Vegas. Even better, she is bringing longtime Insecure collaborator Prentice Penny along for the ride.

HBO has officially ordered a pilot for the currently untitled project, which Rae will write and executive produce. Before everybody starts celebrating another full Issa Rae series on HBO, however, let's make one thing clear: this is currently a pilot order, not a series order. HBO still has to decide whether it wants to take the project beyond that initial episode. But Rae and Penny working together at HBO again? Yeah, you've got our attention.

The comedy centers on Menzel, a 30 year old barber with dreams of becoming a sports manager, whose best friend JB is an emerging professional boxer. As JB's career begins gaining momentum, the two men find themselves navigating ambition, loneliness, insecurity and the complicated ways success can reshape even the closest friendships. Las Vegas and the high pressure world of professional boxing provide the backdrop, but the friendship between these two men appears to be the real fight at the center of the story.

Issa Rae and Prentice Penny Together Again Just Feels Right

Rae writing the pilot is already enough to make this project interesting, but Penny's involvement makes it considerably harder to ignore. The former Insecure showrunner will serve as showrunner and executive producer while also directing the pilot, putting two of the key creative voices behind that series back together.

And no, we're not expecting Insecure: Men With Boxing Gloves. What makes the reunion exciting is the possibility of seeing that same sharp understanding of friendship applied to a completely different group of characters. Insecure was particularly good at recognizing that friendships can be loving, petty, supportive, jealous, complicated and occasionally exhausting all at once. Taking that kind of emotional honesty and applying it to two Black men navigating success in professional sports could give Rae and Penny plenty to dig into.

The premise also puts a different spin on the usual boxing story. We've seen countless projects about fighters chasing championships, surviving brutal training camps and trying to become the next great name in the sport. Focusing equally on the aspiring manager standing beside the fighter gives the project another perspective, particularly if JB's growing success begins changing the balance of a friendship that existed long before anybody cared about his record in the ring.

HBO and Issa Rae Have Some History

Rae's relationship with HBO stretches back to Insecure, which premiered in 2016 and ran for five seasons. She later executive produced A Black Lady Sketch Show and created Rap Sh!t, the Miami set comedy that ran for two seasons on HBO Max. Earlier this year, Rae signed a three year first look film and television production deal with Paramount, though this new HBO project reportedly predates that agreement.

That makes this something of a homecoming without actually being a homecoming. Rae has moved into a new chapter of her career, but there is clearly still room for the creative relationship that helped turn Insecure into one of HBO's defining comedies of the last decade.

No casting has been announced yet, and because we're still at the pilot stage, there is no premiere date to start circling on the calendar. HBO has to give the full series order first, so nobody start asking us when Episode 1 drops.

But Issa Rae writing about friendship again, Prentice Penny running the show and Las Vegas boxing providing the backdrop? HBO, go ahead and shoot the pilot.

We'll be waiting to see if this one makes it into the ring.