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Issa Rae, BJ The Chicago Kid, Victoria Monét and More on How Insecure “Truly Represents the Creatives” Through Music

Ahead of the show’s Season 5 premiere on October 24th, we're looking back at its most iconic music moments

insecure music
Illustration by Steven Fiche
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    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.

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    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.”

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    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.

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    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.”

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