1. Regina Hall
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Remember Due North from season two of Insecure? The show that kept Issa, Tasha, and Chad glued to the TV in this Underground parody starred Hall as Ninny; a house slave who shared a sexual tension with her master (Scott Foley).
2. Ray J
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While on the topic of fictional shows, it’s only right we talk about the “groundbreaking special,” Looking for LaToya. Ray J played Rufus during the season four premiere, the over-the-top love interest who wants everyone to know that although he is not LaToya’s boyfriend, he did, “in fact, hit.”
3. SZA
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The Grammy-nominated artist played LaToya Thompson, the 26-year-old who was last seen at a Red Lobster on July 23, 2019 before she went missing. *Spoiler alert* she was found October 2, 2019 working on a Disney Cruise and became the first black Ariel.
4. Carl Anthony Payne II
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Who better to portray LaToya Thompson’s dad Bryan than the Martin alum?
5. Kandi Burruss
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Wrapping up the LaYoya Thompson family tree is no other than Kandi Burruss or Glenda who is suspicious of Rufus (Ray J).
6. Terri J. Vaughn
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Terri J. Vaughn plays investigative reporter Rose Cranberry. From interviewing Red Lobster employees to revealing what really happened to LaToya Thompson, nothing gets by Rose!
7. Luke James
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A Tinder match with Ben led to Issa — of course — fumbling the bag and an awkward encounter after she couldn’t stop herself from laughing because of his fingers.
8. Sterling K. Brown
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In Season 2, when all hope is not lost for Molly, she meets Lionel; a man who knows what he wants and isn’t afraid to express so. But of course, in true Molly/self-sabotaging fashion, she curves Lionel after he invites her to a SZA concert. We’re also still trying to process what went wrong.
9. Kyla Pratt
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While celebrating her bachelorette party, Dina and her friends spend a fun evening with Issa. That is until she finds out it was part of their bucket list to befriend a stranger and dine and dash. During an Instagram Live, Rae told Pratt that “I wouldn’t be here if it weren’t for you, in every sense of the word.”
10. Jidenna
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Jidenna was introduced as Molly’s love interest Chris back in 2016. He accompanied her to an engagement party where he introduced himself as her boyfriend. After eagerly confronting him on their new label, he disclosed that he was just trying to help after getting the sense that she “really needed a win.” Ouch.
11. Wendy Raquel Robinson
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Although she’ll always be remembered as Malik Wright’s mom, Tasha Mack, from The Game, she played a more mild-mannered and understanding mother to Issa and her brother Ahmal.
12. Erika Alexander
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In season three of the HBO hit series, they introduced Kev’yn — a 90’s black Martin parody — featuring the Living Single star as Yolanda.
13. Bill Bellamy
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From “The Brothers” to “How to Be a Player” and “Cousin Skeeter,” it was perfect casting to have Bellamy play opposite Erika Alexander as Kev’yn.
14. Broderick Hunter
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The model played Felix, Issa’s awkwardly nerdy Tinder match who made it quite clear he wasn’t too impressed with her looks in real life.
15. Ty Dolla $ign
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The R&B singer appeared on the first season of Insecure in Issa’s dreams.
16. Syd
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The Internet’s Syd made an appearance as a DJ for the Kiss-n-Grind party in the season one “Hella LA” episode.
