HotSpot ATL Featured Video

We can all agree the Insecure, HBO’s hit comedy series from the brilliant Issa Rae, is absolutely everything! It’s relevant, relatable and offers a hilarious and heartbreaking look at modern love and relationships. With its second season recently ending and work already being done on the third, Insecure is already a pop culture phenomenon. However, while the character of Issa Dee is hilariously awkward in her quest to navigate the tricky waters of love, friendships and career, let’s not forget those classic TV characters who paved the way.

Long before there was Insecure, there were the classic black TV characters from the plethora of black TV shows from the 80s, 90s and early 00s. Classic sitcoms like Living Single, Girlfriends and A Different World are just a few of the shows featuring female characters that strived to have it all…even if circumstances or themselves kept getting in the way.

Let’s take a look at some of the most iconic TV characters who made it possible for Insecure’s Issa Dee to be so beloved!

Khadijah James – Living Single: Before there was Sex and the City, before there was Friends, there was this iconic 90s sitcom about four friends living in a NYC brownstone (well Max didn’t technically live there) and trying to make their dreams come true. Of the four ladies (including Regine, Sinclair and Maxine) Khadijah James, played by the always amazing Queen Latifah, was the ultimate girl boss of all. She was fiercely independent, often refusing help as she ran her own magazine Flavor, was loyal to her friends, but wouldn’t hesitate to dish out tough love, she often acted as the voice of reason and had just as many problems in her love life as her three best friends. Khadijah James was the perfect example that even those who appear to have it all together, still fall down occasionally as they navigate this thing called life, often with a combination of laughter and tears.

Joan Clayton – Girlfriends: If you were really paying attention during the very first episode of Insecure, then you noticed the cute homage that was paid to the classic series Girlfriends, which Issa Rae has said was a big inspiration for the show. Like Living Single, Girlfriends was also about four friends, but with a more modern millennium take, as the show premiered in 2000. Of all the girlfriends, none were more career-orientated, awkward, neurotic, frustrating, lovable and funny than Joan Clayton, played beautifully by Tracee Ellis Ross. Joan wanted nothing more than to have the fairytale relationship, perfect career and be the ideal friend to everyone—too bad she continued to get in her own way at every turn, ensuring her outcome would be the opposite of what she intended. No matter how many times Joan came up short she always dusted herself off and went full speed ahead into her next adventure…exactly how Issa operates on Insecure.

Whitley Gilbert, Freddie Brooks, Kimberly Reese – A Different World: This trio of ladies from the still relevant and forever iconic TV show A Different World, represented practically all of the emotional, professional and financial ups and downs you face as you become an adult. Whitley, Freddie and Kim were all very different personality-wise, but their awkward, hilarious and at times touching struggles, as college students who eventually graduate and truly begin to face life’s obstacles, were quite similar. Whitley realized that she had to grow up in order to find her Prince Charming, her dream job and have long-lasting friendships. Kim had to learn to make room for her fierce dedication, education, love life and friends to all coexist in the same space. Freddie had to understand that being different and following your own path doesn’t mean that you have to alienate yourself from others and that true friends will accept all your eccentricities. These all are rites of passage that most of us have dealt with at some point, which is why these classic characters will always have relevancy.

Pamela James – Martin: Sure, Gina was the female lead on the legendary FOX sitcom Martin, but she was in a relationship for the entire series, meaning viewers never got to see her as a single girl. This is why her best friend Pam was the one to look to, as she had the most romantic rollercoaster ride of any of the cast members. She was constantly teased about not having a man, but Pam rarely let Martin and his boys get her down for long. Pam was sexy, stylish, sassy and she refused to settle for anything less, which was such a strong testament to 90s female TV characters. Viewers may not have gotten to see Pam get married, although we did get to see her boo’d up with Tommy for a bit, but she didn’t need to be because she was the single representation of two girlfriends while Gina was the committed half—that’s what you call the perfect balance.

Teri Joseph – Soul Food (TV series): Where to begin with Soul Food’s Teri Joseph. She was the classic overachieving, Type-A personality that was the first one to call when you were in trouble, but had the worst track record with love. Twice divorced, but finding unexpected love with a man who was younger and initially worked as a courier, attorney Teri faced multiple obstacles in her relationship—watching closely as her married, younger sisters faced their own troubles. Teri didn’t need anyone and because she was so used to being everyone’s savior it was hard for her to open up and let someone else take care of her. This is a situation that many modern career women face, and although Issa’s Insecure character hasn’t directly faced this issue, her best friend Molly likely has or will soon.

Melanie Barnett – The Game: When it comes to modern TV romances, few characters had as many messy situations, false starts and stops and non-stop drama as The Game’s Melanie “Med School” Barnett. The show’s long-running romantic saga of Melanie and her professional NFL boyfriend Derwin was the most dramatic and addictive part of the series. Melanie made so many mistakes that we all fall victim to in our 20s, but as hilarious and painful as it was to watch, it proved to be so relatable because of its imperfections. From moving cross-country to follow her boyfriend and ultimately finding him cheating with someone else to having a “hoe phase” like Issa and finally marrying her soulmate, Melanie navigated through it all through tears, laughter, her girlfriends and finally learning to stand on her own two feet.

Olivia Pope – Scandal: It may not be a comedy like the other shows, but ABC’s Scandal has enough relationship drama to last a lifetime. Let’s just get it out of the way, Olivia Pope is a boss in every sense of the word (she practically runs Washington,) but her personal life is often in shambles. It once again proves that love is that often tricky area of life where even the most poised and polished of women have trouble. Issa cheated on her boyfriend with an old classmate, while Olivia was having a long-standing affair with the then-married POTUS. Their worlds may be miles apart, but their relationship issues are perhaps more similar than one would imagine. With Scandal nearing the end of its runs, fans are eagerly wondering if everyone’s favorite fixer will get her happy ending.

Mary Jane Paul – Being Mary Jane: While only on the air a few years longer than Insecure, it’s hard not to notice how Mary Jane Paul and Issa Dee both have a lock on who can find themselves in the messiest romance scenarios. Mary Jane may not share Issa awkwardness, but she definitely shares her insecurities of not feeling good enough…in work or in love. Also like Issa, just when you think Mary Jane is finally about to get her rainbow at the end of her storm, the other shoe drops and she’s right back at square one.


Stork Alert! John Legend And Chrissy Tiegen Are Expecting Baby #2

Judge Orders Tyrese To Refrain From Spanking Daughter, Enroll In Parenting Classes

Tyra Banks Makes Triumphant Return In New ‘ANTM’ Teaser Trailer

From Khadijah James To Joan Clayton – Classic Black TV Characters Who Paved The Way For ‘Insecure’  was originally published on

More From HotSpotATL