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

    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.”