As ‘Insecure’ Nears The End, Issa Rae’s Raedio Label is Providing a ‘Starting Point’ For Artists

During the premiere of the fifth and final season of HBO’s Insecure on Sunday evening (Oct. 24), Issa Dee, played by the show’s creator and lead actress Issa Rae, calls it quits with her recently reignited old flame Lawrence Walker (Jay Ellis) while barely getting much of a word in. Walker takes a moment to collect his own words before he stammers, “Yeah. I, uh, know.”

But as the heartbreaking silence between the two lingers, “Fun” by rising rapper and neo-soul singer Nnena breaks it up, playing in the background of the episode’s final scene before the credits roll. The scene leaves the audience wondering if Issa and Lawrence’s short-lived rekindled relationship, a leftover narrative arc from the end of season four, was, as the hook of the song suggests, “just for fun,” or was meant to be extinguished so both characters can finally move on.

Nnena describes “Fun,” which was officially released last Friday via Rae’s record label Raedio in partnership with Atlantic Records as the first single from the show’s upcoming new soundtrack, as “a prime example of a guy stringing you along for a good a– time, then leaving your a– with so many f—ing questions afterwards. You start to question all of your time lost and ask yourself, ‘Was this just for fun?’”

“A bi— got teary-eyed, because I’m like, ‘Da–, this is really happening right now,’ and the timing of the music was perfectly matched,” Nnena tells Billboard in a statement about her song’s placement in the season five premiere, which marks her first major synch placement on television as well as her first-ever soundtrack placement. “I’m so f—ing happy Issa trusted me to add to the vibes, ‘cause sh– got real when [Issa and Lawrence] got out that car!”

The Cleveland-born, first-generation Nigerian-American singer performed “Fun” at a dinner in the show’s stomping grounds of Los Angeles celebrating the final Insecure soundtrack last Friday, jokingly telling Yvonne Orji (who plays Issa’s bestie-turned-adversary Molly Carter on the show) to get her act right before launching into her tender, thought-provoking performance.

“I’m just really excited for her, because it shows what our brand ethos is about, which is showcasing the next generation of talent,” Raedio president and Rae’s longtime business partner Benoni Tagoe tells Billboard over Zoom.

Kier Lehman has been Insecure’s long-standing music supervisor over the Emmy-winning dramedy series’ last four seasons. But Rae employs a very hands-on approach with the show’s song selection, to represent a range of emerging R&B and hip-hop acts such as Yung Baby Tate and Derrius Logan, as well as established stars like SZA and Buddy — all while specifically putting L.A.-based and female artists on the map.

“Insecure and the Insecure soundtrack acts as a tool to break artists or at least introduce people to artists,” Tagoe says. “[Issa has] told me there’s times when she may have picked a song, and she feels like if she watches a cut of Insecure and the song doesn’t fit, it really ruins it for her.”

Not only do the songs come together for a treasured soundtrack for loyal Insecure viewers, but they also soundtrack Issa’s character’s all-too-relatable struggles with adulthood, singlehood in L.A. and Black womanhood. Kari Faux’s “Top Down” plays during Issa and Molly’s awkward backseat ride en route to the girls’ beach trip during the season one finale, while SZA’s “Supermodel” plays when Issa sends a risqué “Tryna f—?” message to a Tinder match as she seeks other fish in the sea post-breakup with Lawrence near the beginning of the second season.

Last Friday, HBO Max, in conjunction with Raedio and Audacy’s Pineapple Street Studios, launched Insecure Interludes, a playlist that mixes music featured on the series with commentary from Rae, Lehman and Ellis, as well as artists featured in the series like Vince Staples, Victoria Monét and Rico Nasty unpacking its cultural impact.

“From the beginning, music has played an integral part in Insecure. The music itself is a character—it’s a friend, it’s a familiar voice and that’s always been the intention,” Rae tells Billboard in a statement. “Music has a way of taking us back to a specific memory or moment in time and I think a lot of people can relate to that when they hear a song on the show. When it came to developing the final soundtrack, I knew Kier and Raedio could capture that feeling and leave our fans with something they can always return to, while also providing a platform for emerging artists to have their voices heard on an international scale.”

Nnena’s “Fun” was helmed at the Insecure writing camp this past spring, where approximately 70 hand-selected artists, songwriters and producers gathered at L.A.’s Hard Pink Studios to collaborate on records that had a shot at being featured on Insecure’s last season. Some of the participants at the camp beside Nnena include Raedio signees TeaMarrr and Josh Levi, who also have secured placements on the season five soundtrack.

“I was happy just to be invited to that camp honestly, that was good enough for me,” Nnena says. “My homie [and producer] Sonic arrived and saw there were no studios left — just empty rooms with tables in them. So he was like ‘F— it,’ and started looking for speakers to bring upstairs, because he came with his Apollo guitar and I high-jacked a mic plus some headphones. We only found one speaker, but we made it work. The first song we cooked up in that room was ‘Fun.’ Then my bro Brandon came upstairs and sprinkled some fairy dust on that intro. After that, we were sure something was gonna happen with this song.”

“We were able to put people in rooms that normally wouldn’t be in a room together, whether that be because of stature of their career at the moment or because they just haven’t crossed paths,” Tagoe describes. “The cool thing about our writing camps is that we have a very high success rate. Because we have a brand that stands for quality music, people know that we have great curation skills, [and] it’s easy for us to be able to get the music done from start to finish in terms of working with the artists and creatives but then also [being] able to place it in things like Insecure, place it in campaigns with Google and Nike. I think the best part of [the writing camp] is we were able to foster a creative environment and then be able to show tangible results from those attendees.”

On top of being able to cash in on those lucrative synchs from Insecure, the show’s featured artists also get sizable engagement on Shazam and streaming platforms. Last October, Niña Dioz’s 2018 single “Salsa” set the mood for the start of Molly and her “Asian Bae” Andrew’s (Alexander Hodge) steamy baecation to Mexico during season four — but things really started to heat up for Dioz’s music.

In a previous Billboard case study, the queer Mexican MC went from having 92 million Spotify followers two weeks prior to the synch to having 374 million two weeks after. “Salsa” also experienced over an 8,500% increase in total on-demand streams in that same four-week time frame.

“The proof is in the pudding. We’ve been able to feature them on Insecure, feature them on our soundtrack, and there’s a clear uptick from the moment that they were featured on the soundtrack or the moment that they were featured on the show,” Tagoe says. “But then there are things that are measurable in terms of street cred. I have conversations all the time with managers, artists, labels and publishers who were just so grateful because we’ve been very instrumental in being able to give an artist their first synch opportunity.”

Raedio has more opportunities beyond Insecure to continue giving up-and-coming acts their big break through synchs. The “audio everywhere” branded company, which bolstered its music supervision department following Raedio’s acquisition of the Bonfire Collective firm in 2020, has been working on music supervision on series such as Epix’s Godfather of Harlem, Starz’s Power and HBO Max’s forthcoming Sex and the City reboot, And Just Like That.

“As we continue to build relationships with those artists, and as we continue to create opportunities within Raedio, we’re always looking to plug those artists,” Tagoe says. “Insecure is the starting point, but it’s definitely not the finish line.”