Hella Glowed Up: See The Cast Of 'Insecure' Then And Now

By Keyaira Boone · Updated October 21, 2021

Insecure introduced us to Black characters who represented our favorite coworkers, closest sorority sisters, and long-lost soulmates. 

The story of Issa Dee and Molly Carter stumbling through the professional and personal challenges sprinkled across the end of their twenties has been illustrated by a cast of characters representing the diversity sorely missing from our primetime lineups five years ago. 

Newer faces like Natasha Rothwell, Sarunas J. Jackson, Tristen J. Winger and Y’lan Noel joined small-screen veterans like Amanda Seales, Jay Ellis and Neil Brown Jr. to bring a group of young successful Black people willing to protect and criticize each other to life. 

Together, the cast tackled topics like postpartum depression, bi-phobia, the gig economy, fractured friendships and the downsides of polyamory with humor and charm. 

Black performers are often relegated to being expositional props tasked with telling the stories of white protagonists. This show gave even the briefest of roles the chance to present fully formed characters. A dedicated gang member was still allowed to be a doting father, a frazzled intern dispensed sage advice and a tryst became a trusted source of refuge. First dates, next-door neighbors, and Lyft passengers each got a chance to tell more of their stories than the sassy Black best friend or silent clique member ever could. The characters were so full that the creator was advised to save some space for a white face or two to avoid alienating the audience.

As the show prepares for its upcoming final season there is no doubt of its legacy as a series that will forever change the landscape of television through the impact of its stories and the way it uplifted Black actors. 

The opportunities to show the range it provided led to more work for the cast in front of and behind the camera. Throughout the show’s five-season run they booked high-profile comedy specials, inked major production deals and nabbed rules in romantic comedies and highly anticipated Blockbusters. 

See how far the cast of Insecure has come since we took our very first trip to the doors of the Dunes five seasons ago below.

01

Issa Rae (Issa Dee)

In 2013 ABC passed on Rae’s comedy I Hate LA Dudes. Then considered a widely successful web series creator, she was having trouble transitioning into mainstream entertainment without compromising her vision. She released a memoir titled after the character who put her in the spotlight in 2015.

02

Issa Rae (Issa Dee)

Awkward Black Girl was a hit and continued to prime audiences for the signature brand of humor that would be found in Insecure when it was picked up by HBO. Today Rae is a six-time Emmy-nominated mogul helping others see their own visions flourish in the beauty, hospitality and of course entertainment industries.

03

Yvonne Orji (Molly Carter)

In 2013 Orji was trying to kick-start her career on her own with roles in short films like Sex (Therapy) with the Jones. Later she created her own series First Gen. The comedienne managed to land her role on Insecure with no agent or big-named manager pushing her to the forefront through her persistence.

04

Yvonne Orji (Molly Carter)

Today she is an Emmy-nominated actress with an HBO comedy special under her belt. She shared what she learned in her journey in the book Bamboozled By Jesus: How God Tricked Me into the Life of My Dreams.

05

Jay Ellis (Martin Lawrence Walker)

Before he was rocking Best Buy blue Ellis made a ton of brief appearances on series including iCarly, How I Met Your Mother, Hart of Dixie and the Bold and the Beautiful.

06

Jay Ellis (Martin Lawrence Walker)

Today, years after he’s perfected the role of the one who got away, he is booking major parts in huge films like the highly anticipated Top Gun: Maverick.

07

Natasha Rothwell (Kelli Prenny)

In 2014 Rothwell was thriving behind the scenes as a writer on Saturday Night Live. She initially came onboard as the recurring cast member who was not afraid to “call bell hooks on you,” in season 1.

08

Natasha Rothwell (Kelli Prenny)

She (and her fraudulent British accent) grew to become one of our favorite parts of the show! She is currently starring in The White Lotus and using her voice to keep our babies entertained on Baby Shark.

09

Amanda Seales (Tiffany DuBois)

Seales has been bringing the funny on the small screen since the early nineties. In 2013 she was on the New York City grind performing and hosting events while developing her own projects.

10

Amanda Seales (Tiffany DuBois)

She represented the bougie friend everyone has to the fullest on Insecure. Today she has successfully hosted a virtual BET Awards; her Smart, Funny and Black brand is thriving; her book Small Doses is on shelves and she has a production deal to create scripted content with Bunim/Murray Productions.

11

Y’lan Noel (Daniel King)

In 2013 King was playing a hip-hop hopeful on the short lived but well written Fuse original The Hustle. A few years later he would be on Insecure showcasing a whole different skill set in the studio.

12

Y’lan Noel (Daniel King)

Noel went from sidepiece to leading man. He will be starring in an upcoming Sam Greenlee adaptation of The Spook Who Sat by the Door and is currently filming A Lot of Nothing.

13

Sarunas J. Jackson (Alejandro “Dro” Peña)

After spending years doing voiceover work and appearing in several videos and short films, Dro popped up in season 2 representing the guy who is perfect in every way—except for that ring on his left hand.

14

Sarunas Jackson (Alejandro “Dro” Peña)

Jackson went on to have roles in Good Trouble, and American Housewife. He is currently starring in the 2nd season of the BET series Games People Play.

15

Tristen J. Winger (Thug Yoda)

Winger whispered his way into our hearts as Baby faced Darius on Rae’s web series Awkward Black Girl. Prior to that he worked as a music supervisor on the True Friendship Society.

16

Tristen J. Winger (Thug Yoda)

Since teaching us not to let a good ‘bouch’ go to waste and exhibiting proper parenting methods for anti-Crip households, he has appeared on the BET series Bigger and 50 Central. He recently completed filming of the upcoming Breaking Tradition.

17

Dominique Perry (Tasha The Bank Teller)

Perry held it down as Shonda in the movie Get Hard before she showed us that if we don’t appreciate our man Tasha will. She also appeared in Public Library, American Hero and The Sin Within.

18

Dominique Perry (Tasha The Bank Teller)

Perry held it down as Shonda in the movie Get Hard before she showed us that if we don’t appreciate our man Tasha will. She also appeared in Public Library, American Hero, and The Sin Within. Since Lawrence introduced her character to his inner f-boi Perry has been booked and busy. She booked roles on shows including Snowfall, Underground, and Black Jesus.

19

Christina Elmore (Condola Hayes)

Before she was dropping a baby-sized bomb on the newly reunited Issa and Lawrence Elmore appeared in the heartbreaking Fruitvale Station. The Harvard grad also had an ongoing role in the TNT drama The Last Ship.

20

Christina Elmore (Condola Hayes)

Today she is starring in the BET series Twenties. She recently completed filming of the upcoming Under The Bridge.

21

Neil Brown Jr. (Chad Kerr)

Before serving up quality ho logic Brown Jr. was a working actor racking up credits on shows including ER, Army Wives, The Walking Dead, Weeds, NCIS and American Dad!

22

Neil Brown Jr. (Chad Kerr)

He continues to dispense wisdom on Insecure and is also a series regular on the show Seal Team. He will appear in the upcoming horror flick The Knocking.