My First Time: Issa Rae Says 1st YouTube Rap Sparked Success

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There aren’t too many places you can turn at the moment and not see the Black and beautiful billion-dollar smile of A-list Hollywood siren Issa Rae. Over the span of a decade, the 38-year-old multi-hyphenate in Black entertainment has created a still-rising career for herself as an in-demand actress, screenwriter, film producer and all-around habitual entrepreneur.

It all began just a decade ago with the viral success of her hit YouTube web series, Awkward Black Girl, where she went from doing cringe-worthy raps on the Internet like this…

To currently flexing on the world at large like this…

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RELATED: My First Time: SleazyWorld Go Walks Us Through His Debut Viral Success

We were blessed to have the Insecure star check in for our latest “My First Time” to give her take on what it was like going viral in those hilarious debut freestyles — it only took a little bit of liquid courage from Moscato to pull it off! Given her recent Barbie fame and the brick and mortar success of Hilltop Coffee + Kitchen, we think it’s safe to say she outgrew the awkward phase.

Watch Issa Rae below on the latest episode of “My First Time”:

• My First Time: Tyrese Gives An Honest Hot Take On The Many Firsts To Come From His Divorce
• My First Time: Coco Jones Tells Us About Her First “Treat Yo’Self” Splurge
• My First Time: Marsha Ambrosius Explains How Jodeci Influenced Her Debut Live Performance

My First Time: Issa Rae Explains How Debut YouTube Rap Led To Success was originally published on ioneblackamericaweb.staging.go.ione.nyc