Issa Rae: From Awkward to Insecure to 8 Figures

Insecure is ending but it is not the last you’ll be seeing Issa Rae, she’s here to stay.

In March, it was announced that Issa Rae and her Hoorae media label inked a 5 year overall deal with WarnerMedia. This deal gives HBO, HBO Max and Warner Bros. television exclusive rights to Rae’s work in TV plus a first look film deal with all of WarnerMedia brands including New Line, HBO Max and Warner Bros. Pictures Group. In Rae’s Variety cover story interview when explaining why she signed the five year deal with HBO wittily said, “They wifed me up”. I’d say “I do” too with this deal! According to Variety the deal is valued at $40 million.

As Insecure comes to an end with it’s fifth season premiering later this year (no date yet), Issa Rae will still be very busy co-producing shows like A Black Lady Sketch Show that just premiered its second season on HBO Max and a new series, “Rap Sh*t” that’s in pre-production. “Rap Sh*t” will be a half-hour comedy on HBO Max about two estranged high school friends from Miami, Shawna and Mia who reunite to start a rap group. The series will be starring Aida Osman (Crooked Media Podcast host), Jonica Booth (Bad Girls Club), and KaMillion (Love & Hip Hop: Miami) and co-executive produced by rap duo City Girls, JT and Yung Miami. Hoorae also has a docu-series on the way, “Seen & Heard” that will explore the history of Black television. There’s more in the works but these are just the projects they can talk about.

Issa Rae’s endeavors doesn’t just stop at television and film although I mean, she is an award winning actress. Rae took home the NAACP Image Award for Outstanding Actress in a Comedy Series for her role as Issa Dee in hit series, Insecure. Insecure also won the NAACP Image Award for Outstanding Comedy Series but, it also should’ve won an award for outstanding music because WHEW they have us bobbing our heads up and down every episode! You can thank Issa for that because she created Raedio, a music label that does publishing, original sound score, and music supervision. Raedio is responsible for the soundtracks for all of Hoorae’s projects including Insecure. Which is cool because Rae can have the best of both worlds working with more than one of her passions at a time. Issa Rae wears many hats, she’s the actress, the producer, the writer, the music supervisor, and her hair is poppin’ from her haircare line Sienna Naturals!

Yes, that’s right Issa Rae even co-owns a haircare brand! Sienna Naturals was founded by Hannah Diop, a longtime friend of Rae’s, so she saw the brand come up from the very beginning. Issa Rae became the face and co-owner of the brand in 2020.

Issa Rae, born Jo-Issa Rae Diop is building an empire and it all started from High School theatre then on to Stanford University then on to creating and starring in the Youtube series, The Misadventures of Awkward Black Girl (which according to Rolling Stone, she got production help from a fellow Stanford classmate Tracy Oliver, the writer of Blockbuster comedies Girls Trip and Little). Now, Rae is teaching aspiring creators all she’s learned being the amazing creator she is on Masterclass. What doesn’t Issa Rae do!?

The award winning multi hyphenated actress is also piling on magazine cover on magazine cover! So far, this year Issa Rae has been the cover star for Variety, Rolling Stone, and Paper Magazine. Check out the IG posts below to prove it.

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