Season 3 Wine Downs

Something Insecure knows how to do is ignite conversation across the social sphere. As the third season of the hit comedy got underway, HBO wanted to give fans more of what they love: insight into the mind of creative powerhouse Issa Rae. This thinking — paired with a desire to lean into the buzzworthy topics each episode presents — inspired a fresh approach to behind-the-scenes video: the Insecure Wine Down. Taking a note from Rae’s own practice of “wine-ing down” with her closest friends, Season 3 revamped the concept to feature both Issa Rae and showrunner Prentice Penny as poolside hosts of the weekly, episodic series. Accompanied by guests from the cast, sangria and bright sunshine, the Wine Downs focused on the key themes and personal experiences that informed the episode’s creation and performance. The organic conversation led to candid commentary and insights into the personal mishaps that informed some of the characters’ “questionable-like” decisions.

Each piece had a social-first teaser, where the cast and hosts played “truth or dare,” with questions that related to the show, driving buzz and promoting the longer videos. This fun, relaxed take on behind-the-scenes content became staple viewing for Insecure viewers, who looked forward to new installments following each new episode of Season 3.