As fans and critics digest the meta homecoming in the latest episode of Insecure, which returned for its fifth and final season on Sunday in the same way both Issa Rae and Issa Dee returned to their shared alma mater, much has been spoken about growth—the growth of the show’s characters as well as its cast and creators, and how that growth has brought the young adults portrayed on-screen and those watching at home back to familiar places. What could be added to that conversation is the growth of the artists whose music soundtracked the show’s first four seasons, as their careers ballooned at the same rate as Rae’s after having their earliest songs featured in her hit dramedy.
A key component to the richness of Rae’s depiction of Black millennial life in Insecure is the intuitiveness of her taste in music. As she’s gone on to launch her own label, Raedio, under Atlantic Records, it should surprise no one that her show has a history of including songs from a number of emerging artists before they scored their biggest hits. With the help of music supervisor Kier Lehman, Rae has forecasted a handful of pop culture’s most ubiquitous sensations. Below is a list of the most notable times she and her creative partner pulled this off.
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SEASON 1
Vince Staples, “Norf Norf”
Episode: “Thirsty as F**k”
Airdate: October 30, 2016
Before: Staples became a mainstay on the soundtracks of big-budget motion pictures, such as Black Panther, Spider-Man: Into the Spider-Verse, and Queen & Slim.
The music in the earliest episodes of Insecure established a formula that the series would follow for the rest of its run. Stars of the moment like Drake and Kenrick Lamar are heard throughout the first few episodes, as well as stars of the past like D’Angelo and Kelis, but sonically the show feels the most grounded when it’s platforming stars in the making like Vince Staples. Not only is the end-credit placement of Staples’ first hit, “Norf Norf,” an example of this, but its opening lyric perfectly syncs with the title and theme of the episode—“Bi**h, you thirsty, please grab a Sprite.”
Jorja Smith, “Where Did I Go?”
Episode: “Shady as F**k”
Airdate: November 6, 2016
Before: Smith reluctantly became the face of “whisper singing,” a thirst tweet obsession, and the alleged inspiration for Drake’s “Jaded.”
Fans may be hard-pressed to remember a time when Jorja Smith was known more for her artistry than the unrequited affection she inspires from lusty men online and rappers 10 years her senior, but a rewatch of Insecure will remind them of how smitten music lovers once were with her songs. Smith’s signature sound—soulful and subdued in a way that, in all fairness, features less whispering than the internet may have you believe—also feels like a signature of the show’s tendency to sometimes use subtle, jazzy music to transition between scenes.
Chloe x Halle, “Red Lights”
Episode: “Real as F**k”
Airdate: November 20, 2016
Before: Both sisters ascended to solo stardom, with Halle being cast as Ariel in Disney’s upcoming live-action remake of The Little Mermaid, and Chloe’s take on the “Buss It” challenge going viral months before the release of her debut single.
At the time of this episode’s air date, Chloe x Halle were best known as the precociously gifted sisters who signed to Beyonce’s Parkwood Entertainment after going viral for their cover of “Pretty Hurts.” They were still a year away from establishing themselves as series regulars on Grown-ish, let alone multi-hyphenate talents capable of singing, writing, producing, dancing, and even dressing circles around their popstar peers. The inclusion of this record from Chloe x Halle’s very first EP is evidence of Kier Lehman and Issa Rae’s impeccable taste and foresight.
SEASON 2
Cardi B ft. Offset, “Lick”
Episode: “Hella Great”
Airdate: July 23, 2017
Before: Cardi’s star-making single “Bodak Yellow” became a cultural sensation, topping the Billboard Hot 100 for three consecutive weeks, receiving Grammy nominations for Best Rap Performance and Best Rap Song, and eventually becoming the first song by a female rapper to sell over 10 million copies.
Season 2 was when the stars aligned for Insecure, and the show established a habit of platforming new artists within weeks of them becoming the most celebrated acts in music. The best example of this is Cardi B’s “Lick” being heard in the season premiere less than a month after she released “Bodak Yellow,” a song that grew to be so popular GQ and Rolling Stone both named it one of the defining songs of the decade—not the year, the entire decade.
SZA ft. Travis Scott, “Love Galore”
Episode: “Hella Great”
Airdate: July 23, 2017
Before: SZA received five Grammy nominations for CTRL, as well as a wave of critical acclaim that resulted in her debut LP appearing on more year-end lists than almost any other album of 2017.
The very same episode that features “Lick” also features this song, which was released about six weeks prior to the episode’s air date and earned a spot on Rolling Stone’s list of The 500 Greatest Albums of All Time. Of Insecure’s prophetic placements, this one feels the most true to its narrative identity, as SZA’s freshman opus deals with similar themes of feeling lost, lovesick and plagued with self-doubt as a 20-something-year-old Black woman. Perhaps an even better example of this synergy is the placement of “Supermodel” in the very next episode (aptly titled “Hella Questions”). On the song and during the episode’s final scene, SZA sings, “Why I can’t stay alone just by myself? Wish I was comfortable just with myself,” as Issa scrolls Tinder for a late-night hookup not long after a cryptic sexual encounter with her ex.
Lizzo, “Fitness”
Episode: “Hella Blows”
Airdate: August 27, 2017
Before: The slow-burn success of “Truth Hurts” and subsequent overnight interest in Lizzo’s body and lifestyle turned the singer into the most needlessly controversial artist in recent memory.
In a way, an early song from Lizzo being heard in “Hella Blows”—two years before the re-release of “Truth Hurts”—is fitting. Like the singer herself, the episode is funny, hyper-sexual, permanently memorable, and an inexplicable trigger for online debate. While today Lizzo is best known as a nexus point between disingenuous discourse regarding health, fatphobia, and body politics, there’s something syncretic about rewatching this episode (which ironically features a song from her called “Fitness”) and feeling her presence as Insecure tackles the direly serious topic of blowjob etiquette.
SEASON 3
City Girls, “Where The Bag At”
Episode: “Better-Like”
Airdate: August 12, 2018
Before: The duo attracted fanfare (and at times an appropriate level of controversy) as the most unapologetically raw rap chicks this side of Cardi B.
Airing one month after the City Girls provided additional vocals on Drake’s “In My Feelings” (and were partially name-checked during the song’s chorus), the Season 3 premiere of Insecure found itself in lockstep with two rappers who define what’s truly fun about the show better than any other. If SZA speaks to the sides of Issa and Molly that are most prone to feelings of loneliness and confusion, the City Girls represent the sense of chaotic misadventure that comes whenever the characters attempt to bond and bounce back. “Better-Like” and “Obsessed-Like,” which also features a City Girls song, are both underscored by Issa and Molly turning to each other on the heels of uncomfortable romances. In “Better-Like,” the two link up for a “party Lyft” following some awkwardness that Issa encounters with Daniel and Molly experiences with Dro. And in “Obsessed-Like,” they get together and pop up at the home of roommates Nathan and Andrew, after the former ghosts Issa and the latter ruins a date with Molly by playfully insulting her. This is hands down the most City Girls-esque season of the series (period!).
Snoh Aalegra, “Fool For You”
Episode: “Ready-Like”
Airdate: September 16, 2018
Before: Aalegra dethroned Jorja Smith as the queen of “whisper singing,” eventually releasing better-received albums than Smith and drawing favorable comparisons to Sade.
Even though it’s likely coincidental, there’s something to be said about the fact that Season 2 is the last time we hear Jorja Smith on Insecure, and Season 3 marks the first time we hear Snoh Aalegra. If nothing else, this particular placement feels predictive of the way Aalegra’s rise would eventually market correct Smith’s worth as a whisper-singing commodity. Even though both women are stars in their own right, and they both make sublimely sultry songs that suit the scenery of Insecure well, it’s a plain fact that Snoh Aalegra is a better vocalist. Part of the show accurately anticipating trends means it at times predicted which artists would wind up stepping into another’s lane.
Victoria Monet, “The Glow”
Episode: “Ghost-Like”
Airdate: September 30, 2018
Before: Monet’s critically acclaimed Jaguar EP and her two Grammy nominations for her contributions to Ariana Grande’s Thank U, Next album culminated in a breakout year for the singer-songwriter in 2020.
Victoria Monet’s “The Glow” is the only song on this list thus far that appeared on an official Insecure soundtrack, meaning it’s evidence of an even sharper sort of intuition, as it was commissioned two years before Monet would achieve mainstream success as a writer and performer. The intentionality with which the song is placed is palpable. Throughout this season, Issa’s living situation and relationship status are both in limbo, as she tries to find a way off Daniel’s couch and later has to cope with being ghosted by Nathan. Yet in the closing sequence of the season finale, she all but rejects Nathan’s attempt to re-enter her life and finally settles into her new apartment. This full-circle moment is punctuated by the upbeat groove of “The Glow,” as Monet sings, “Now that I got my sh*t figured out, I kind of love it.”
SEASON 4
An argument could be made that it’s too soon to tell whether the artists who were heard throughout Season 4 will stand the test of time, as it’s only been a year since the show’s penultimate set of episodes first aired. However, a few of them do show promise.
There’s Young Baby Tate, whose two songs on Insecure’s official soundtrack for the season came around the time the Atlanta rapper announced she’d signed a deal with Raedio. Elsewhere, viewers hear from R&B rookie Giveon, whose record “World We Created” was featured in the episode “Lowkey Trying” a month after he sang on Drake’s “Chicago Freestyle.”
Emerging songstress Baby Rose also crooned her way onto the show, with her song “Show You” being played as Issa and Lawrence passionately remove each other’s clothes and rekindle their love in “Lowkey Happy.” And rounding out the season’s relatively new voices is Moses Sumney, whose somber ballad “Keeps Me Alive” scores the aftermath of Lawrence and Condola’s bombshell pregnancy reveal in “Lowkey Lost.”
There’s no telling whether any of these artists have what it takes to sustain lasting careers. But if Insecure’s track record provides any indication, it’s safe to assume we’ll hear them again throughout the show’s final season and beyond.