Issa Rae’s ‘Insecure’ Getting Syndication Run on OWN

Insecure Season 4 (Credit: HBO)

HBO’s award-winning comedy series Insecure is coming to OWN in February, via a new syndication deal.

OWN announced the agreement on Friday, saying episodes from the show’s original run will air on the network, including the pilot. To mark the occasion, OWN released a trailer promoting the dramedy’s arrival.

Insecure was created by Issa Rae and Larry Wilmore. The series explored the Black female experience through best friends Issa (Rae) and Molly (Yvonne Orji). The cast also included Jay Ellis, Natasha Rothwell, Amanda Seales. and Kendrick Sampson.

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The series was inspired by Rae’s acclaimed web series “Awkward Black Girl.” It premiered in 2016 and concluded its run in 2021, after five seasons.

Executive producers on the HBO series included Issa Rae, Prentice Penny, Melina Matsoukas, Michael Rotenberg, Dave Becky, Jonathan Berry, and Amy Aniobi. Prentice Penny served as showrunner.

The show won a Primetime Emmy in 2020 for Outstanding Single-Camera Picture Editing for a Comedy Series. It also picked up multiple NAACP Image Awards over the years, including for Outstanding Comedy Series.

Warner Bros. Discovery and Harpo Studios property OWN delivers programming for African American audiences, so Insecure is a natural fit.

The series uplifted the Black culture and highlighted Black-owned businesses around Los Angeles.

On June 11, 2021, Rae took to social media to let fans know the final episode had been shot.

“Said goodbye to some of my favorite people on Earth, on and off screen, this past week. Never imagined all the doors this would open. Forever grateful to those who paved the way for us to do us,” she captioned the post.

Insecure debuts on OWN with back-to-back episodes, starting in order with the season one pilot on Tuesday, Feb. 7 at 9:00 pm ET/ PT.

Below are details on the episodes rolling out this February:

Tuesday, February 7 at 9:00pm ET/ PT – Episode #1: “Insecure as F**k”
In the wake of her 29th birthday, Issa Dee (Issa Rae) reconsiders her dead-end relationship with Lawrence (Jay Ellis), her live-in boyfriend. Meanwhile, Issa’s best friend, Molly (Yvonne Orji), mourns her singledom and the state of her “lady parts.” Later, Issa uses an open-mic night as an excuse to reconnect with an ex. Written by Issa Rae & Larry Wilmore; directed by Melina Matsoukas.

Tuesday, February 7 at 9:45pm ET/ PT – Episode #2: “Messy as F**k”
After the unexpected events of the previous night, Issa (Issa Rae) tries to decide what to do about Lawrence (Jay Ellis), while sticking to her plan to embrace a bolder side of herself. Molly (Yvonne Orji) treats herself to a “fancy day” and goes on a promising date. Lawrence gets advice from an unexpected source. Written by Issa Rae; directed by Cecile Emeke.

Tuesday, February 14 at 9:00pm ET/ PT – Episode #3: “Racist as F**k”
Issa (Issa Rae) and Lawrence (Jay Ellis) try to move past their issues at home, as she deals with her colleagues’ doubts and he gets a reality check from a head hunter. Molly (Yvonne Orji) introduces Jared (Langston Kerman) to her friends, and later struggles to give words of wisdom to a new summer associate at work. Written by Dayna Lynne North; directed by Melina Matsoukas.

Tuesday, February 14 at 9:45pm ET/ PT – Episode #4: “Thirsty as F**k”
Although things are better than ever with Lawrence (Jay Ellis), Issa (Issa Rae) turns to Daniel (Y’lan Noel) for help during Career Day. Molly (Yvonne Orji) finds herself in a tough position when a partner asks her to give Rasheeda (Gail Bean) a talking-to. Facing disappointment at his new job, Lawrence bonds with a surprising confidante. Written by Laura Kittrell; directed by Kevin Bray.

Tuesday, February 21 at 9:00pm ET/ PT – Episode #5: “Shady as F**k”
Issa searches for a way to get her open mic video taken down; Issa reconnects with Daniel; Lawrence faces questions about his future with Issa; Molly invites her “perfect guy” to a coworkers engagement party. Written by Ben Dougan; directed by Melina Matsoukas.

Tuesday, February 21 at 9:45pm ET/ PT – Episode #6: “Guilty as F**k”
Issa tries to keep things together while hiding her guilt; Lawrence gets serious about his commitment to Issa; Molly embraces a new relationship. Written by Amy Aniobi; directed by Debbie Allen.

Tuesday, February 28th at 9:00pm ET/ PT – Episode #7: “Real as F**k”
Issa deals with drama at a work fundraiser; later, she clashes with Molly over life choices. Written by Prentice Penny; directed by Kevin Bray.

Tuesday, February 28th at 9:45pm ET/ PT – Episode #8: “Broken as F**k”
A girls’ trip finds Issa and Molly in close quarters, while Lawrence vents with his boys. Written by Issa Rae; directed by Melina Matsoukas.