Insecure's Season 5 Soundtrack Opened a World of Opportunities For New Artists


For five seasons, Issa Rae’s runaway hit Insecure has given us a host of things to talk about and even more to listen to. The groundbreaking HBO series emerged in 2016 intending to share authentic Black stories, but it’s accomplished so much more since then. Before Insecure came along, music had become an afterthought for some TV shows. But Insecure elevates music through storytelling and has provided so many opportunities for rising artists to make their presence known in the music industry.

The show itself is a significant contributor to Rae and her team’s entire creative brand, and from that, other entities have been born. Raedio – the record label and audio-everywhere company cofounded by Rae with Atlantic Records – is an extension of Insecure’s work in music. The label, which launched in 2019, has signed promising acts like Josh Levi and TeaMarrr, giving them a platform to amplify their music. Levi – a singer who got his career start acting in Los Angeles – is just one of many artists who have flourished under the Insecure umbrella. Singing is a craft he’s been perfecting since he was 5 years old, and it’s taken him to high places like The X Factor, where he was introduced to millions of people. However, Raedio and Atlantic gave him the foundation he needed to support his unconventional artistic vision.

“My point of view is not linear in any way. Raedio has always been really supportive of that and given me the resources to bring that to life, and also understand and see my vision,” Levi told POPSUGAR. “So that combined with Atlantic has been such a dope combination. And then also Issa Rae is a legend and I’m the biggest fan of her. So having someone, a cultural tastemaker and influencer of culture, like her on my team and behind me is surreal.”

“I always used to say early on that this show might be trash – but the music was for sure going to be fire.”

Beyond being a Raedio artist, Levi is one of many who had the privilege of being featured on one of Insecure’s five soundtracks. As a self-proclaimed “major music fan,” Rae always aimed for the music in her HBO comedy to be perceived as more than stellar. “I always used to say early on that this show might be trash – but the music was for sure going to be fire,” she remarked on the intro of Insecure Interludes – a Spotify playlist that combines inside commentary with some of Insecure’s most memorable songs. “Like I was very confident in that.” With that goal in mind, Insecure‘s soundtracks have grown to be larger than life. They’ve planted seeds for systems like Raedio to spark a fire under talent who didn’t even know they needed an extra push.

Singer-rapper TeaMarrr – the first artist to join Raedio at its inception – always dreamed of becoming an actress. But Raedio and Insecure gave her a reason to explore opportunities elsewhere. “Music was something that I did in the shower, something that I was hella shy about,” she said. “I was dating rappers, musicians, trumpet players, and refused to sing in front of them. But when I started to dive into music in Toronto – without any judgment from my peers, because I’m in a new country where no one knows me – I was able to really open that musical vibe. I always wanted to be independent, and Issa’s an [actress]. So when she reached out, I was like, Oh my God, maybe this is the gateway to my acting world.”

TeaMarrr said Raedio and Atlantic have both helped her immensely in her career so far. She saw clear results of how their support could take her to new heights after her song “Cool Enough” was featured in episode four of Insecure’s fourth season. “I remember seeing the Shazams for ‘Cool Enough’ when it got played on season four,” she said. “All the other Shazams were like 200, 300 [requests], but ‘Cool Enough’ was skyrocketing at like 7,000 in one night. I was like, whoa. That was really cool to see the Shazams go up and people were looking out for me – Masego even slid in my DMs because of [that song]. Insecure is like this super-exclusive musical hub now, like if your music plays there, you’re legit. So it’s really cool to be a part of that class.”

Insecure as a whole has given a big push to well-established artists, offering them another chance for people to fall in love with their music. That list includes Thundercat, Rico Nasty, Jazmine Sullivan, Saweetie, SZA, and many more who credit the show for being a grand stage for creativity, especially when it comes to showing love to its LA-centric roots. But at its core, it remains a place for any and all up-and-coming artists to try to get their shining moment.

It remains a place for any and all up-and-coming artists to try to get their shining moment.

In its final season, Insecure has brought on newcomers like Cleveland rapper, singer, and songwriter Nnena and uplifted them in ways they never imagined. The budding artist had the honour of closing out the first episode of season five with her song “Fun” – a moment she said was a shock to her. “I’ve been watching that sh*t since my junior year [of college],” she said. “I’m like, yo, I’m really in this b*tch. Like damn, this sh*t is really happening. If you watch the show, then you get the feeling. You can understand a little bit of [what I’m] feeling.” From that placement on Insecure alone, Nnena’s career kicked into overdrive. She’s more than excited to soon share all of the dope opportunities that have come her way since – including being featured on the series’s season five soundtrack alongside Levi and TeaMarrr.

Aside from soundtracks, Insecure has found other unique ways to turn itself into a launching pad for artists – specifically through The Sync Up campaign. The contest launched in May of this year and helped emerging musicians get their music featured on the show’s final season. According to Raedio President Benoni Tagoe, the campaign started as a story of Insecure’s DMs. Many artists and producers would reach out asking how they could be a part of the show. From there, it evolved into an interactive pipeline for undiscovered talent and a way to let people in on the show’s fascinating music process.

Insecure has also opened up its own writing camps focused on catering to the show’s many stories – an experience that TeaMarrr describes as a “fun circus.” “Issa takes real raw advantage of the artists that are hungry, in a good way,” she said. “They come there and they pour their all, and a lot of them aren’t signed. A lot of them are writers [who] just want to be in the room, and now they have a credit to a song that’s in a show. It’s so beautiful to see.”

Insecure is the game changer that put other TV shows on notice. In the last decade, we haven’t seen a show shift the cultural landscape quite like the HBO series. Some praise it as the blueprint for Black creators – a true testament to starting from the bottom and completely taking over. And when it comes to music, the show found a way to bring it to the forefront – this time as a main character. “I think Insecure has trailblazed and pioneered being intentional with music,” Levi said. “Issa was definitely one of the first to really be intentional about crafting the sound to coincide with the stories she was telling through the characters, and I’ve seen that so much more with a lot of shows today.”

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