Over the past five years, we’ve seen Issa Rae’s iconic Insecure character Issa Dee through it all. Between the break-ups, stalking potential baes on Instagram, and having to furnish a new home with no money to her name, Issa has been a voice of her millennial generation. Amid the ups and downs of adult life, Rae has portrayed a millennial in an all-too-relatable manner, alongside a killer soundtrack.
Since the inception of her YouTube series Awkward Black Girl, Rae has aimed to make music “a character” in all of her projects. On HBO’s Insecure, which premieres its fifth and final season this Sunday (October 24th), we see Issa experience wins and losses, with many scenes tied to a specific song.
Over the years, Rae, composer Raphael Saadiq and music supervisor Kier Lehman have used the show to spotlight up-and-coming hip-hop and R&B acts. During the breaks between writing seasons, Rae and Lehman would discover songs and put them in playlists and folders for consideration to include in the show. Some of Rae’s favorite artists that she’s discovered over the past five years include Rico Nasty, Sampha, Lion Babe and Kari Faux.
Faux has had at least one song placed in at least one episode each season, and Rae credits the singer-songwriter as her muse for the first season. “Even before [Insecure] got greenlit, I remember hearing [“No Small Talk”] on [Childish Gambino’s] mixtape [STN MTN / Kauai], and then being obsessed with Kari Faux,” Rae tells Consequence. “She embodies so much of the energy of this show.”
In Season 1, we see Issa question her relationship with her boyfriend of five years, Lawrence (Jay Ellis). Throughout these eight episodes, Issa struggles to make an impact in her job at a student outreach program, is at odds with her best friend, Molly (Yvonne Orji), and later cheats on Lawrence with an old fling from high school, Daniel (Y’Lan Noel).
When Issa confesses to cheating on Lawrence, Lawrence stays at a friend’s place before ultimately deciding to move out of their apartment in the season finale. When Issa discovers Lawrence has packed his belongings and left, she and Molly sit down on a couch she and Lawrence previously discarded outside. Molly embraces Issa as she breaks down; BJ The Chicago Kid’s “Heart Crush” plays as the season closes out.
“Heart Crush” was inspired by an actual ex of BJ The Chicago Kid’s, but seeing it in this scene gave the song a whole new meaning. “It was an artistic moment for me,” BJ says. “Hearing my song as I’m seeing what’s going on, and how they [incorporated] my real life into their acting world… I think for me to see it in a raw format, that encouraged me to make more music that can match more moments like that.”
By Season 2, Issa is still heartbroken over her breakup with Lawrence, but tries to move on by meeting men on apps. Rae cites SZA as her muse for this season, and recalls the singer-songwriter sending her a pack of songs before her major label debut album CTRL dropped. The pack included “Drew Barrymore,” “Love Galore” and “Supermodel,” the third of which can be heard in the second season’s first and second episodes.
“I still say we could have placed every single song from [CTRL] in Season 2,” Rae says. “That was just a gift.”
We hear “Supermodel” at the end of Season 2’s second episode, as Issa has decided to move on from Lawrence, check out dating apps and send a message reading “tryna fuck” to one of her matches. By the third episode, she finds a friend in her neighbor Eddie, played by singer-songwriter/producer Leon Thomas III.
Though Thomas’ music doesn’t actually play in the series until the Season 3 finale, Thomas enjoyed working with Rae, and even admits they had a good laugh in between takes shooting sex scenes. He recorded the Buddy-assisted “Favorite,” along with the rest of his Genesis EP, with hopes that Issa would choose at least one of the songs to be featured on the show.
“It’s definitely a true representation of manifestation,” Thomas tells Consequence, “and it turned out that Issa actually really loved the song and ended up putting it on the show. I’m just really thankful for the whole thing. I feel like Insecure represents a creative taking the wheel in her hands and really driving a whole generation into a moment.
“I think it’s awesome that Issa has been able to represent creatives who can do it all; write, produce, and act. There [are] so many elements that she was involved in that made it special. I feel like Insecure truly represents the creatives.”
By Season 3, Issa and her friends are all going through major life changes. Issa quits her job, Molly starts working at a new law firm and Tiffany (Amanda Seales) is pregnant. As Tiffany progresses in her pregnancy, the friendship dynamic between her, Molly, Issa and Kelli (Natasha Rothwell) changes, most notably when Tiffany doesn’t ask the ladies to help plan her baby shower, which leads to a confrontation at the event.
After Kelli confronts Tiffany, Victoria Monét and Lucky Daye’s “Little More Time” can be heard as the ladies re-enter the party. Monét and Daye had no plans for the song when they initially recorded it; however, music manager Rachelle Jean-Louis sent the song to Lehman, who placed it in this scene, which Monét would find more relatable three years after its airing, following the birth of her own daughter.
“I understand it more now than before,” Monét says. “I didn’t get to have a baby shower, because of the pandemic, but going through those motions, I can understand how sometimes a baby changes friendships. It was a really cool and relatable scene that I look back on retrospectively.”
In the Season 3 finale, Molly and Kelli take Issa to an outdoor screening of The Last Dragon for her 30th birthday. Throughout the episode, Issa is upset with Nathan (Kendrick Sampson) for having ghosted her for a month. When Nathan and Issa meet up, and Nathan explains his absence, Issa decides not to pursue a relationship with Nathan, in order to figure out what she wants.
The season closes with Issa furnishing her apartment, as Monét’s remixed version of Willie Hutch’s “The Glow” from The Last Dragon plays, indicating a new chapter for Issa. Rae specifically asked Monét to create an updated version of “The Glow” for this particular scene.
“I kind of had to just recreate a song that already exists and add some kind of nuances that fit with the present day and time,” Monét says. “I wasn’t able to see the scene before, but they gave me super clear direction and I sent them a version [of “The Glow”]. Issa made a lyric change, and I re-recorded that part, and then that was it. They know what they want musically and so they were very clear with me on what they needed from the song.”
Music has been omnipresent throughout Insecure, but the fourth season proved to be the most musical yet. Much of it is centered around a block party that Issa and Condola (Christina Elmore) organize in Inglewood. The party takes place during Season 4’s fifth episode, and features performances from SiR and Vince Staples. While planning a star-studded episode may seem daunting, Issa says the hardest parts about the episode were “the night shoots, and fighting with Molly.”
Lehman, however, remembers having difficulty clearing SiR’s performance of his song “Mood.”
“I think there was a sample [in the song] that hadn’t been negotiated,” Lehman says. “We had a hard time finding the sample owners. And that one wasn’t cleared very much up until the last minute, maybe even over past the last minute.”
Also appearing in the block party episode is rapper Aminé — not as himself, but as Darnell, a love interest of Kelli. “I think a lot of people know that I’m not really down to play an artist, or play stereotypical roles,” Aminé says. “So for me, if I’m going to do something [on screen], I would love a challenge. Getting to play Darnell was really fun.”
Aminé’s role was a long time coming, as he had been shouting out Rae and Insecure on tracks for years, including on his 2017 track “Squeeze,” when he proclaims he’s “practicing my verse up in the mirror like I’m Issa.” Rae has also appeared in Aminé’s video for “Spice Girl,” and included his song “Blackjack” in Season 3’s Coachella episode.
Rae and Aminé first connected via Twitter in 2017, following the release of his debut album Good For You, as Rae was lauding the album over a series of tweets. The two later DM’d, and Aminé remembers Issa as “a genuine person” from their first encounter. “It didn’t really feel ‘industry’ when we chatted,” Aminé recalls. “I was just talking to a regular person.”