Issa Rae is at the beginning of her self-proclaimed "mogul era." The multihyphenate has a first-look deal with Warner Media, a burgeoning audio production company, a media production company, co-owns a coffee shop in Inglewood, co-founded a management company, and has three productions in development. The Emmy-nominated actor is executive producing "Rap Sh!t," a new HBO Max series about a female rap duo that has garnered rave reviews and set social media aflame, much like "Insecure."
Music has always played an integral role in Issa Rae's work, dating back to when she was a college student making parody music videos. From J’s freestyles in the "Misadventures of Awkward Black Girl" to the alternative R&B jams soundtracking "Insecure," to the Miami bass and sexy freestyles of "Rap Sh!t," each of Rae’s projects contains strong musical ties that support and elevate the story, while simultaneously introducing viewers to new artists. Thanks to her elite musical curation and dedication to authenticity, Rae’s trailblazing productions have become something of a musical zeitgeist defining how to use music in visual media in the 2020s.
Music played a supporting role in Rae's journey to household name. In the mid-aughts when YouTube and Facebook were on the verge of breaking big, Rae was a Stanford University student with a dream, a love of entertainment, and a determination to make her own lane. During her time there, she created and produced a few different projects, including a mock reality show about Black student life at Stanford called "Dorm Diaries." The "Real World"–inspired series was shot on a microbudget and released on Facebook.
"The first video got around 150,000 views before I made it private, but there were students from all over the country watching and engaging," Rae said in an interview with the News House.
Rae didn’t have the budget to hire a music supervisor for the mini-series, so she used songs like Busta Rhymes’ and Mariah Carey’s suggestive duet "I Know What You Want," and an instrumental of Dr. Dre’s "F— You" to amp up the drama or add levity to scenes. After graduation, Rae planned to pitch the series to MTV and BET, but her apartment was broken into and her camera equipment, laptop, and scripts were stolen, forcing her to pivot in another direction.
The ambitious star continued attending networking events, which presented their own challenges for the self-proclaimed introvert. After braving it through a particularly awkward event, Rae had a eureka moment that would change her life: She would make a show about a Black woman who was awkward, much like herself, and "The Misadventures of Awkward Black Girl" was born. No stranger to tiny budgets, Rae set about finding a crew to shoot the web series and would flex some major multitasking skills as the show’s lead actor, producer and writer — the latter role requiring her to pivot into a songwriter.
Staying true to her love of music, the pilot episode opens with J, played by Rae, driving while rapping to a song called "Booty Shawts," by fictional group the Doublemint Twins. A few of the group’s raunchy tunes appear in the first season of ABG, including "I Love my Man" (feat. Lil' Light Squin’) and "Take my Panties off" (feat. Bruce Illest).
The series similarly used licensed music to support the storytelling: Ice Cube’s "You Can Do It" plays as J daydreams about being the star dancer at a house party, while "Jungle Fever" by the Chakachas sets the cheeky tone for her first date with a white man named Jay. The series was an instant success, catching the attention of Pharrell, who offered Rae and co. a deal. His company, iamOther, aired the second and final season of "Awkward Black Girl" on its YouTube channel in 2012.
With her star on the rise, Rae linked up with Shonda Rhimes to develop a show for ABC called "I Hate LA Dudes," but the network ultimately passed on the project because it wasn’t a good fit for their family-friendly roster. Rae went back to the drawing board in 2013 and began working on the "Insecure" pilot with Larry Wilmore, a prolific film and TV writer, and two years later, HBO greenlit the first season of the show.
The groundbreaking series showcased Inglewood and other parts of the Los Angeles area often overlooked by Hollywood, while highlighting emerging local artists. Rae has been transparent about using music to assist her storytelling and fully understands how to wield its power — music can drive a narrative forward, convey the emotional intent of a scene and evoke an emotional response from the audience. Rae’s masterful merging of music and storytelling has translated to success. Over the series’ five-year run, "Insecure" was valued for its soundtrack as much as its writing, cinematography, and social media discourse.
The show’s music supervisor, Kier Lehman, shares Rae’s point of view on the marriage of music and storytelling. "We connect [music] with this story that they’re already kind of really invested in this show or a movie," he told Rolling Stone. "It really makes a deeper connection and helps people remember this music in a new way and have a new sense of memory for the scene or for the way that they made them feel or the way that it connects with their real life."
"Insecure" spotlighted established R&B singers like Jasmine Sullivan and Bryson Tiller, alongside up-and-comers like Michael Snead, Kari Faux, and TT the Artist. Alternative R&B often served as the backdrop for the show's love scenes — a purposeful decision meant to move the audience. "We put sex scenes and Black lovemaking on the map in a new way," Issa told the LA Times. "I love adding music to those scenes, deciding which ones will affect how the audience may feel. Episode 8 of the last season, I always say that’s my opus because I wanted every song to represent the romanticism."
In October 2019 during the latter half of "Insecure's" run, Rae took her passion for music a step further by partnering with Atlantic Records to launch her own label, Raedio. "Music has always been an essential part of every project I do and working with emerging talent is a personal passion," Rae said in the press announcement. "Raedio allows me to continue that work within the music industry and audio entertainment space."
Music by singer-rapper TeaMarrr, Raedio's flagship artist, was featured on "Insecure." (Rae also appeared in the music video for "Kinda Love," the singer’s debut single for the label.) The burgeoning imprint has since added Baby Tate to its roster, supervised the music for HBO Max’s "Black Lady Sketch Show," and created an emerging artists program in partnership with Google.
After spending five years in front of the camera on "Insecure," Rae opted to take a step back and produce the next project in her overall deal with Warner Media. Set in Miami, "Rap Sh!t" follows two estranged friends (played by Aida Osman and KaMillion) who join forces to create a female rap duo, much like the City Girls (whose Yung Miami and JT are executive producers the show, and one of their unreleased tracks will be featured in an upcoming episode).
"[City Girls] were so generous with lending us original music and helped to consult about their own Miami influences while we were getting started," Rae tells GRAMMY.com.
Authenticity was a priority for Rae and "Rap Sh!t" showrunner Syreeta Singleton, who recruited other Miamians to join the writers’ room, consult on shooting locations, and pen original freestyles for the leads to perform. "We were really, really intentional about making sure the writers’ room was reflective of people who came from here," Rae told Essence magazine. "The goal was to make sure that people who are from Miami watch it and recognize themselves and their city."
When crafting the show’s musical direction, Rae took inspiration from the current crop of female emcees. "This era was inspired by every single female rapper who has created music right now," Rae continues. "But my playlist while writing included Flo Milli, Latto, Meg Thee Stallion, Cardi, Nicki, Lightskinkeisha, Baby Tate... the list goes on and on." Adds Sarah Bromberg, one of the show’s music supervisors and a VP at Raedio: "Female rappers, in general, are all over this show. You'll hear cues from Enchanting, Big Boss Vette, Asian Doll, Kali, KentheMan, Rubi Rose... too many to name!"
Freestyle rapping, whether in front of the mirror or a group of onlookers, is a staple of Rae’s work, and "Rap Sh!t" maintains this tradition. Since the show’s main characters Shawna and Mia are budding music stars — and not amateurs like the characters in "Awkward Black Girl" and "Insecure" — Rae and the team decided to enlist the help of songwriters, producers, and professional emcees to craft the duo’s freestyles and bars.
"The music supervision team started the process with weekly meetings with Syreeta during the writing of the show. We discussed what songs we were going to be developing, what the plot points were, and what we wanted our sound to be," Bromberg says. "Then, Raedio put together a writing camp in L.A. with a limited and select group of songwriters and producers. We sent briefs to the camp for each of the show songs discussed in our weekly meetings. Most of the original songs you hear this season were written at that camp. Afterwards, we continued to develop, shape and polish the songs with a few of the writers from the camp."
Rae also expressed interest in bringing in one of her favorite female emcees, Dreezy, to craft Shawna’s lyrics. "Benoni Tagoe [the show’s music consultant and President of Raedio] helped us seal a deal with her, and she did a lot of the polishing and writing of raps scripted in the later episodes," Bromberg explains. "We also brought on Danja as the vocal producer for the season. He tracked and produced Aida and KaMillion and helped us shape their sound as Shawna and Mia."
Rae praises the team at Raedio and "Rap Sh!t’s" leads for their roles in the development process. "I was particular about the show's sound and Raedio was incredible about curating camps to create original music for the show and soundtrack. It was generally very collaborative and we all understood that the music had to be great." Rae continues, adding that Danja lent his studio to the production and worked with the actresses extensively to refine their sound. "We were fortunate to have musically inclined actresses in Kamillion, who actually does this, and does this well, and Aida, who is absolutely gifted and so smart with her bars and incredibly witty."
A few of Rae’s other favorite female emcees — NCognita, and pineappleCITI — also helped craft lyrics for the show’s freestyles and studio sessions. Osman and KaMillion, an emcee in her own right, deliver the lyrics throughout the season’s eight episodes with high energy, charm and swagger.
Rae’s dedication to showcasing authenticity and layering music into her storytelling has paid off. The soundtracks for the various seasons of "Insecure" have racked up millions of streams and ushered alternative R&B into the mainstream, and the music of "Rap Sh!t" is already receiving rave reviews. By highlighting emerging artists in her work, Rae’s productions have become a platform for music discovery, introducing audiences to up-and-coming artists that are pushing the culture forward with their innovative works.
How Issa Rae Created A Platform Where Black Music And Art Could Thrive