Issa Rae

Do Issa and Prentice know the characters on #Insecure? #issarae #bloccparty

The birth charts are unofficial... but the evidence is convincing 😂 #bloccparty #issarae

Issa & Prentice Respond to Insecure Fan Questions & Wild Theories

Why is Amanda Seales not on Issa Rae's Insecure: The 10th Anniversary Tour?

Inside Somerville: Issa Rae's Love Letter To South Central LA

You never know you're making a classic while you're living it. Kyla Pratt talks Love & Basketball 🏀

Issa & Prentice Talk Love & Basketball, LA Accents & Hollywood Staying Power with Kyla Pratt

Birthdays will have you lit and spiraling at the same time 🥲

Issa Rae’s ‘Insecure’ anniversary tour is coming to Las Vegas

Issa Rae's 'Insecure' anniversary, Paradice Festival with Kaytranada, Ricky Martin and more Las Vegas events on sale this week

The Insecure: 10th Anniversary Tour is coming to your city! 🍾 Tickets on sale now!

This one had us in tearssss 😭 Hear more about how Issa’s Hoe Summer inspired BrokenAF

Issa & Prentice Talk Finale Reactions, #LawrenceHive & Bad Breakups

Why We're Still Talking About ‘Insecure’ & Looking Forward To Issa Rae's 10th Anniversary Show Tour

Issa Rae Brings Her ‘Insecure’ 10-Year Anniversary Tour to Oakland

Issa Rae announces tour celebrating 10th anniversary of ‘Insecure’

Issa Rae, Prentice Penny Embarking On ‘Insecure: 10th Anniversary Tour’

Celebrate 10 years of INSECURE with us — live on stage! Tickets on sale now!

Picture This: Branden Cook, Alex Isley, Julian Horton, Meagan Good & More Pitch the Funniest Shows

Issa Rae to celebrate 10 years of 'Insecure' with anniversary tour stop at The Met

Issa Rae Announces "Insecure: The 10th Anniversary Tour"

Issa Rae bringing Insecure anniversary tour to Las Vegas this fall

Issa Rae to celebrate a decade of ‘Insecure’ with multi

Y’lan’s been on an all-time villain run ever since 😭

And the rest was TV history 🥲 Yvonne, Issa and Prentice take us back to the beginning of Insecure

Yvonne is in the building!! 🎉🥳 watch newest episode of Blocc Party out now!

Issa & Prentice Talk Toxic Friendships, HBO Sex Scenes & Becoming Molly with Yvonne Orji

If Molly's dating life felt a little too real, that's because it was. Hear Issa and Amy discuss

One thing about Drake lyrics: they were going to find their way into the conversation somehow. 😭

Before it became a show people quoted, it became a conversation Issa wasn't ready for

Hear Issa and Prentice explain how real dating stories found their way into S1of Insecure

Best of Picture This: Kyla Pratt, Lil Rel, Mero, Meagan Good & More Share Hot Takes & Funny Stories

Issa Rae Clarifies Comment on Women Not Settling Down With the 'Best D*ck'

Issa & Prentice Talk Mt. Rushmore of Black TV, Y2K Reality Shows & First TV Crushes

The kind of confession that makes the whole room pause. 👀 #issarae #insecure

Before it became part of the culture, it was just a name on the table. 📝

Hollywood gets into the microdrama race as mobile-first storytelling draws stars and major studios

Issa Rae & Taye Diggs Lead Microdrama Boom

Issa & Prentice Talk Debbie Allen, Jared’s Sexuality & Guilty Flashbacks

Issa Rae, Lena Waithe & more on women behind the lens | ComplexCon(versations)

Issa & Prentice Talk Cheaters, Checklists & Circling the Block

PICTURE THIS: Kyla Pratt on Navigating Child Stardom, Rejection & Her Next Dream Role

Chanté Adams and Issa Rae's powerful scene

BTS Of Issa Rae's Cover Shoot | UnCovered

Issa & Prentice Talk ABG Lore, Messy Molly & Building the Insecure Writer’s Room with Amy Aniobi

Issa & Prentice on Thirsty Women, Y’lan Noel’s Abs, & #BrokenP**sy

Tell Me Lies' Branden Cook Shares His Truth On Acting, His Relationship & Fame

Watch Keke Palmer Convince Issa Rae She’s Joining a Cult in Hilarious Prank Call

How Melina added Solange to help turn Insecure into a destination for discovering fresh voices 💜

May 28, 2026