Issa Rae, Ella Mai and cast of ‘Insecure’ host ‘Wine Down’ at Essence Fest

Issa Rae (Photo credit: Charmyonne Bailey)

HBO hit show “Insecure” hosted a “Live Wine Down” at Essence Fest this year. The popular comedy series’ creator, executive producer and star, Issa Rae, sat down with TV bestie Yvonne Orji and showrunner Prentice Penny to recap the end of season two and raise the curtain on the upcoming season.

“Insecure Wine Down” is a weekly series where Rae sits down with a guest — usually a fellow cast member or someone involved with the show — to sip wine and discuss their thoughts about what happened in the latest episode. The concept stemmed from get-togethers where Issa Rae and her group of friends would bring bottles of wine and “talk s— about our work week. It was literally a wine down,” says Rae on the first episode of the series.


The event at Essence Festival kicked off with a performance by Ella Mai singing four of her hit singles and dedicating each song to a specific “Insecure” character or relationship.

As the new season premiere approaches, Rae and Penny discussed challenging decisions made regarding the season two finale. “Even in the writer’s room, that was a big point of contention between some of us [about] whether or not Issa should go back to Daniel and Molly should go back to Dro. We just wanted to reflect that these are real-life things,” Rae explained. For season three, “we are very excited to explore new dynamics and characters and new relationships,” she added.


Before premiering the season three trailer, Rae announced that Crissle West from “The Read” podcast and Francheska Medina (@HeyFranHey) from “TheFriendZone” podcast will be returning for the “Insecuritea” podcast, where they dissect each episode and lend their perspectives.

“Insecure” cast members in attendance were Y’lan Noel, Sarunas J. Jackson and Lil Rel Howery. Others guests included attorney and political commentator Angela Rye, actresses Tichina Arnold and Tisha Campbell, comedienne and “The Real” talk show host Loni Love, and former NFL wide receiver Devale Ellis and his wife Khadeen Ellis.

Season three of “Insecure” premieres Aug. 12 at 10:30 p.m. EST on HBO.

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