The Stunning Transformation Of Issa Rae

Issa Rae is a multi-talented force of nature, excelling in acting, writing, producing, and even in her business ventures. Rae got her start while studying at Stanford, parlaying a web series into a seriously enviable TV and film career. But she wasn't always so sure she was on the right path. "Did I have to pay hundreds of thousands of dollars to make YouTube videos?—that was embarrassing for me," she confessed to Glamour.

The "Insecure" creator and actor began performing as a child in school plays in Potomac, Maryland, but she was also always writing plays for herself and her pals. While she hit a bit of a rough patch in middle school, she found her footing attending a predominantly Black high school in Los Angeles where she was inspired and encouraged by the work of other Black writers.

Rae is known to recreate her own lived experiences, from her earliest web series to her Emmy-Award winning HBO show, and through her work her fans can see her glow up from the awkwardness of her twenties to the insecurities of her thirties. And aside from her creative projects, the multi-talented performer has also been passionate about giving back to her community. Issa Rae has come a long way from school plays and is now a bona fide movie star, and her career just keeps on picking up steam. Read on to learn more about the stunning transformation of Issa Rae.

Issa Rae was born Jo-Issa Rae Diop in Los Angeles, California in 1985. Her father was a doctor and her mother was a teacher, so she came from a family of high achievers. Rae moved around a bit during her childhood, spending some time in her father's native Senegal, but it was in elementary school in Potomac, Maryland that she began writing and acting.

When Rae was in the fifth grade, she was cast in a school production of "A Midsummer Night's Dream." She was chosen to play the role of Demetrius, and Rae's mother took issue with that. "My mom was like, 'What the — they're gonna cast this little black girl as a boy?'" Rae shared with Backstage. But Rae wasn't deterred, as up until that point she'd only put on plays she'd written for herself and her friends. Playing Demetrius was a new experience, and one she enjoyed. "But I really liked it, and my teachers were really encouraging, and it was my first time kind of performing [and] acting someone else's words," Rae explained.

Issa Rae is the star and co-creator of a show called "Insecure," but in real life, she comes off as anything but. The multi-talented actor is poised, self-assured, and vibrant in interviews and on the red carpet, but there was a time in her young life when her confidence took a hit. Like a lot of kids, it was during her tween years that Rae began to have issues with her self-esteem. "There was a certain age where I was like, 'I know I'm the sh*t,'" Rae told Glamour. But when it came time for middle school, she started to look at herself differently. "... I was like, 'Oh, I'm not attractive to other people. The guys I go after don't see me that way,'" Rae said.

Rae also recalled being made fun of for her hair back in those days, telling NPR, "I remember one girl saying to me just that nobody should fight me because I would probably take something out of my nappy hair and throw it at them..." Even though these insults stung, Rae had to admit there was an inherent humor at the root of them. "They were really funny, though," she said. "They were just jerks, but they had a very specific sense of humor."

By the time Issa Rae was in high school, her family had moved from Maryland back to Los Angeles. It was there that she attended King/Drew Magnet High School of Medicine and Science, where she was no longer one of the only Black kids in the student body. Rae was still very much into writing and performing, and attending a predominantly Black school helped open her eyes to artists and writers she previously hadn't heard of.

Rae credits one of her teachers with introducing her to inspiring new material. "My English teacher, who was also the drama teacher, used to find these hidden-gem black plays, and there was just something about seeing the medium for us..." she explained to Backstage. Those plays helped Rae feel seen, and also validated her goals to write and perform material that was meaningful to her. "...it was, 'This is specifically written for us.' As a creator and as an actress, I felt fulfilled in terms of trying to do that on that level," Rae shared.

After graduating from high school, Issa Rae was off to the prestigious Stanford University where she majored in African and African American studies. It was during her college years that Rae really began mining her own experiences for her creative projects. "Nobody's you," she told The Hollywood Reporter. "How you exploit that as a creative means so much." Being a Black student at a mostly white college provided Rae with the material to create her first web series, "Dorm Diaries."

The show was presented as a mockumentary and starred Rae's friends and fellow students. It was thanks to the growing popularity of social media that Rae was able to find a larger audience for her projects. Her series found a home on YouTube and Rae used Facebook to connect with those outside of her circle of friends. "Even though I hate it now, Facebook was the sh*t for me back in the day, just because of the audience that I was able to build...," she told Backstage.

While "Dorm Diaries" featured storylines poached from Rae and her friends' real lives, her goal was larger than showcasing these experiences. "[Writing] in college became about: I wanna create because there are no opportunities for us," she explained. "The plays at the time didn't resonate with Black kids."

Issa Rae graduated college in 2007, and several years later, she launched another web series, this time appearing on the other side of the camera. "The Misadventures of Awkward Black Girl" made its debut in 2011, featuring Rae in the starring role. The series was a hit, showcasing Rae's talent as both a writer and an actor. But it also served a more important purpose for the star. "The Blackness [in the show] was at the forefront, but the humor and awkwardness were universal and that is an archetype that is not often represented," Rae told Vogue.

The success of "The Misadventures of Awkward Black Girl" led to Rae being offered a deal with HBO, for which she created the wildly popular series "Insecure." Again, Rae was drawing upon her own experiences, but this time she was presenting a more mature version of herself. "'Awkward Black Girl' is the early twenties version of me kind of getting comfortable in my skin. 'Insecure' feels like the late twenties, early thirties version of myself," Rae explained. "Insecure" ran from 2016 until 2021 and garnered plenty of critical recognition, including multiple Emmy Award nominations.

In 2018, Issa Rae added video vixen to her ever-growing resume when she made a cameo in Drake's video for his single "Nice for What." Rae called the experience "a dream come true" but not necessarily because she'd been dying to work with the famous rapper Drake. It was the video's director, Karena Evans, who really inspired Rae, and the two became friends. "We are really in a renaissance of black women getting opportunities and shouts to [Drake] for recognizing [her] 'cause she's elevated his videos," Rae told Billboard.

Rae appeared in the video alongside other talented Black performers, including comedian Tiffany Haddish (who used to habitually crash weddings), actor Tracee Ellis Ross, ballet dancer Misty Copeland, and actor Yara Shahidi. The video was much more focused on female empowerment than some of Drake's previous work, such as "Best I Ever Had," which was directed by the controversial rapper Kanye West. Rae didn't hold back while sharing her opinion on that particular video, which featured hyper-sexualized depictions of female athletes. "What the [expletive] was that video?" the actor said.

Much of Issa Rae's creative work has served a dual purpose, allowing her to express herself while also providing positive representation for the community at large. When Rae branched out into an entrepreneurial endeavor in 2019, she seemed to be driven by a similar principle.

Rae and her business partners opened Hilltop Coffee + Kitchen in various Los Angeles neighborhoods, and Rae's inspiration came from her desire to have a local coffee shop in which to do her work. "I live in a predominantly Black neighborhood ... and I always had to leave my neighborhood to go and work in a coffee shop and that didn't sit right with me...," Rae shared with Ebony.

Hilltop's locations in View Park-Windsor Hills, Inglewood, and Glassell Park did well even during the Covid-19 pandemic, according to Rae. She told Barista Magazine, "Hilltop has been pretty innovative in terms of tapping into the community and using its reach to help the neighborhood." While Rae wasn't always on hand to work the espresso machine behind the counter, she knew the work she was doing was important and that Black-owned businesses deserved a chance to thrive. "That is especially essential ... with gentrification comes pushing out the people who have lived there the longest..." Rae explained to Ebony.

In 2019, Issa Rae took on yet another project, becoming the executive producer for HBO's "A Black Lady Sketch Show." Rae teamed up with actor and screenwriter Robin Thede to bring the show to life, and it was yet another hit, earning a multitude of Primetime Emmy nominations and picking up several wins.

The sketch comedy show featured a super talented cast of characters and guest stars including Angela Bassett, Patti LaBelle, Laverne Cox, Quinta Brunson, and Issa Rae herself. According to Rae, everyone was on board to appear on the show, so long as they could work it into their schedules. "Everybody was just super excited to be a part of it, super game, and it shows in every sketch," Rae said during an appearance on "Today."

It would seem that Rae would have been an old pro after starring on "Insecure" for several years, but she was still nervous when it came to her own appearances on "A Black Lady Sketch Show." "It was intimidating," Rae admitted in conversation with Robin Thede for Showmax. "But it was so much fun."

Issa Rae is notoriously private when it comes to her personal life, but in 2021 she wed businessman Louis Diame. Rae had a secret wedding ceremony in the South of France. Rae had planned to keep her nuptials on the down low, but she had been photographed by the designers at Vera Wang in her wedding gown and felt that she wanted to be the one to post the photos first. According to Rae, it wasn't that the wedding was secret, but it wasn't something she wanted to share with the public. "...everybody who was invited knew what was going down, so there was no big, like, keep it under wraps," she shared during an episode of the "The Tamron Hall."

Diame appeared on an episode of "The Misadventures of Awkward Black Girl," but it's unclear if that's where he and Rae first met. In 2019, Rae was spotted wearing a diamond ring on the cover of Essence, but she never confirmed her engagement. But Rae did open up a bit about her married life, telling Self, "I'm extremely happy," in 2021. Rae also reflected on whether or not she planned to have children, citing her busy work schedule as a reason to really think it through. "I know it's not the proper mentality to think that kids will slow you down, but I do feel that way," she revealed.

In 2023, Issa Rae starred in "Barbie," as Madame President Barbie, no less. While she was thrilled to be cast in the role by the film's director, Greta Gerwig, she was worried about looking the part. "After 'Insecure' was done, I willingly let myself go," Rae told The Guardian. "And then instantly, when I found out I got Barbie, I was like: 'Oh no! I gotta look like one!'" Gerwig's aim for inclusivity when featuring her Barbies put Rae at ease, but she did reflect on why her first instinct was to lose weight. "I think it's just that we've internalized so much about Barbie ... it has become representative of the perfect female body," she explained.

Rae dove into the role, even getting the chance to help design one of her Barbie's outfits, and the film was a huge hit at the box office. The one issue Rae had with the Barbie experience? The ubiquitous pink that dominated both the movie and its press tour. "I hate the color pink," Rae admitted. "I've never thought that I looked good in pink..." Despite her dislike for the trademark Barbie color, Rae rallied like a true professional. "But I've been taking one for the team!" she told The Guardian.

2023 was a big year for Issa Rae. In addition to appearing in "Barbie," she also lent her voice to two different projects: the film "Spider-Man: Across the Spider-Verse" and the TV series "Young Love." Working on "Spider-Man" was a thrill for Rae, as she had been a fan of the superhero since childhood. "...to be a part and play Spiderwoman, no less ... in this incredibly multicultural world has been more than a dream come true," she shared with Ebony.

For Rae, the foray into voice acting was interesting and presented somewhat of a challenge. She was accustomed to using her physicality to convey emotion in her acting, and relying on her voice alone made her wonder if the character was coming across in the correct way. "I'm such a big facial expression person so ... not feeling certain they'd be able to replicate that on screen..." Rae told Essence. But in the end it was all worth it. "It's so much fun... to see it all come together," she said.

Issa Rae has never been one to shy away from serious issues, be it the gentrification of traditionally Black neighborhoods, the need to amplify marginalized voices, or fighting to close the gender pay gap. In February 2025, the actor and writer took a stand and canceled her appearance at The Kennedy Center once it was announced that Donald Trump had installed himself as the institution's new chairman.

Rae was not the only celebrity to act following the news, as both musician Ben Folds and "Grey's Anatomy" creator Shonda Rhimes both resigned as artistic advisor and treasurer of the board, respectively.

Rae was set to appear in "An Evening with Issa Rae," described by The Kennedy Center's Instagram as "a night of cozy ambiance, big laughs, and all the nostalgic feels," which had sold out. But she pulled the plug on the event, announcing the cancellation via her Instagram Stories. Rae's statement made clear why she was pulling her event from the venue, citing, "...what I believe to be an infringement on the values of an institution that has faithfully celebrated artists of all backgrounds through all mediums..." (via Vulture).