Wine Down: Hella Great

Wine Down: Hella Questions

Wine Down: Hella Open

Wine Down: Hella LA

Wine Down: Hella Shook

Wine Down: Hella Blows

Wine Down: Hella Disrespectful

Wine Down: Hella Perspective

Wine Down: Better-Like

Wine Down: Familiar-Like

Wine Down: Backwards-Like

Wine Down: Fresh-Like

Wine Down: High-Like

Wine Down: Ready-Like

Wine Down: Obsessed-Like

Wine Down: Ghost-Like

Wine Down: Lowkey Feelin' Myself

Creator and star Issa Rae and showrunner Prentice Penny break down the first episode and how they’re setting the tone for the rest of the season.

Wine Down: Lowkey Distant

Creator and star Issa Rae and showrunner Prentice Penny sit down with Yvonne Orji to unpack Molly’s relationship with Andrew and Issa’s friendship with Condola.

Wine Down: Lowkey Thankful

Creator and star Issa Rae and showrunner Prentice Penny are joined by Christina Elmore to discuss Condola and Lawrence’s interesting first Thanksgiving together and debate whether or not it’s possible to be friends with an ex.

Wine Down: Lowkey Losin' It

Creator and star Issa Rae and showrunner Prentice Penny sit with Natasha Rothwell to discuss the shifting dynamics within the friend group.

Wine Down: Lowkey Movin' On

Issa Rae, Prentice Penny and Jean Elie discuss Issa and Molly’s blowout fight as well as the dynamic between Ahmal and Kelli.

Wine Down: Lowkey Done

Issa Rae and Prentice Penny unpack Issa’s mindset after her fight with Molly at the block party.

Wine Down: Lowkey Trippin'

Issa Rae and Prentice Penny are joined by Alexander Hodge to talk about what Molly and Andrew learn about themselves and their relationship during their first vacation together.

Wine Down: Lowkey Happy

Issa Rae, Prentice Penny and Jay Ellis dive deep into the unfinished business Lawrence and Issa have with each other.

Wine Down: Lowkey Trying

Issa Rae and Prentice Penny are joined by Kendrick Sampson to discuss Nsthan's lingering feelings for Issa and destigmatizing mental illness.

Wine Down: Lowkey Lost

Issa Rae and Prentice Penny sit down with Amanda Seales to unpack the finale.

Wine Down: Reunited, Okay?!

Wine Down: Growth, Okay?!

Wine Down: Pressure, Okay?!

Wine Down: Faulty, Okay?!

Wine Down: Surviving, Okay?!

Wine Down: Tried, Okay?!

Wine Down: Chillin', Okay?!

Wine Down: Choices, Okay?!

Wine Down: Out, Okay?!

Wine Down: Everything Gonna Be, Okay?!

Insecure: The End

Insecure: In the Room

5 Strategies for Dealing with Clueless Coworkers

5 Unlikely Sources of Inspo

5 Break-Up Survival Tips

Final Season Documentary

Looking back at five memorable seasons of Insecure's messy relationships and hella personal growth, this documentary finds creator/star Issa Rae and others reflecting on the hit series.