Okay, so I’ll admit I don’t love pigeon-holing Ashley Blaine Featherson-Jenkins as being a star only in “Black” Hollywood with the title that I chose. Her talent, which we’ll dig into, is not confined to her ethnicity, as she’s a force to be reckoned with across Hollywood—period.

Yet I used “Black Hollywood” anyway. Why? Because I personally see “Black” Hollywood as a compliment not a detriment. To me, being a star in “Black” Hollywood intrinsically means you probably overcame some stuff to make to a career in this industry and the culture still stands with you because you did it without selling your soul, by staying true to your roots, and not trying to transcend into something you’re not.

Which brings me back to Ashley Blaine Featherson-Jenkins, who is truly a one-of-a-kind actress. She does so much as an actress, producer, singer, speaker, and now podcast host. She’s been featured in notable shows like Dear White People, Run the World, Grand Grew, and Bad Hair. However, I first saw her in the famed Black&Sexy web series, Hello Cupid, which she also co-created. To see her go from that, which was no mediocre project, but a web series nonetheless, to one of the more visible Black figures in Hollywood has been amazing journey to watch—and yet, she’s only just getting started.

Ashley’s Early Life and Background

Born Ashley Blaine Featherson, she is a native of Gaithersburg, Maryland. She started acting at school at the age of 4, eventually working her way up to performing at Washington D.C.’s Studio Theatre while in high school.

From there, she wouldn’t travel far at first, going on to attend college at Howard University. There she opted for majoring in musical theater. In an interview with Vibe, Howard was more than just a place to get her education and hone her craft. It was also a place for self exploration. It was at Howard, after a lifetime of relaxer, that she first began her natural hair journey. She was really inspired by all of the beautiful Black woman on campus that had natural hair, and Ashley then vowed that she would never chemically process her own hair again. That obviously is not an easy thing to adhere to as a Black actress, who as a part of the profession, has to do so many different things with her hair to portray a character, look or image.

Ashley’s Early Beginnings as an Actress

Ashley Blaine-Featherson’s earliest roles include a couple of short films (Bonds, Davide’s Reverie) and guest spots on various Black TV shows. Her first significant role was on the aforementioned Hello Cupid, a series that she co-created with Lena Waithe and co-starred in with Hayley Marie Norman (Kenan, Dollface) and Brandon Scott (Dead to Me, This is Us). Hello Cupid was ultimately about a dark-skinned Black woman who was having trouble with online dating and decides to replace her picture with that of her light-skinned friend and roommate. Instantly, she sees more interest from male users, but of course, she essentially falls for someone after having wrongly depicted herself as someone she’s not, which leads to all kinds of confusion, embellishments and arguments.

As I said before, I absolutely loved this show, and there’s no doubt that Ashley was the leading lady in this one. It’s been close to 10 years since I first watched it, and I still recall how well Ashely portrayed “Whitney”, the dark-skinned online dater. She did such an amazing job of communicating the frustration, self-doubt, and hopeless romantic disposition of her character. And yet, as the series evolved, she was able to transition her portrayal into tho strong-minded and loving person her character was becoming.

Hello Cupid, and Ashley’s performance in it, was honestly what made me a big fan of web series, and ultimately led to me creating the first Black web series of my own. As someone who was pretty well-versed in Hollywood, and in particular, low-budget, indie film making, I was taken a back by how awesome a production could be put together on a seemingly shoestring budget. But with Hello Cupid, Ashley, and the cast and crew at Black&Sexy, they were able to pull of something amazing, that if it didn’t change Black digital series all together, it certainly had a profound affect on me.

Ashley Blaine Featherson in Dear White People

The 2013-2014 era of web series was a crazy time. At that point, it had been going fairly strong for about 3 or 4 years, largely on YouTube, and we were starting to see it become a jumping off point for several stars, like Issa Rae with “Awkward Black Girl”, Ben Sinclair and Katja Blichfeld with “High Maintenance”, and Ilana Glazer and Abbi Jacobson with “Broad City”.

Essentially, every aspiring writer, director and actor was trying to make their mark with a web series, and Hello Cupid was no different. Lena Waithe, Ashley’s co-creator on Hello Cupid, would go on to get a few TV writing gigs, which ultimately led to her creating and writing The Chi.

Ashley Blaine Featherson, seemingly more focused on the acting side of things, saw her work on the Hello Cupid Black web series rewarded with what some might say was the opportunity of a lifetime. In 2014, she would have a key role in the Justin Simien independent movie Dear White People. This would be Ashley’s first acting gig in a feature-length film, and she definitely brought her best work to the film. Her role as “Joelle”, or “Curls”, the freedom fighting, intelligent, and ambitious loyal friend to “Sam” (the main character), was essential the plot of the movie, which would go on to gross over $4.4 million at the box office. Ashley’s characters plot line largely involved playing second-fiddle to everyone, despite often being the smartest most motivated among the group, but her inability to speak-up, as well as some undertones of colorism, often kept her from being the center of attention that other members of her friend group often dominated. One of my favorite “Curls” lines from the movie that embodies her activism spirit:

I’m still here. And please know that I will be showing up on McRib day in a Shirley Chisholm T-Shirt sans internal conflict.

Ashley Blaine Featherson as “Joelle Brooks”

While at $4.4 million the movie was no blockbuster at the box office, it was a hugely critical success. In October of 2014, this was the movie every Black person I knew was trying to watch. It had premiered at Sundance earlier that year, and anyone who saw it swore that the movie was a much watch for the social commentary and brilliant direction of the film. And while certainly it had those elements, it was Ashley Blaine Featherson who undoubtedly deliver a stellar performance as part of an unbelievably stellar film that will forever be a classic Black movie.

As was (is?) the times, when something is a classic, we have to remake it. So, the powers that be at Lionsgate, the studio that bought the movie at Sundance, turned the film into an original TV series for Netflix during the height of the Netflix Originals hype. Ashely was able to reprise her role as Joelle, this time with a much more nuanced and developed role that included a backstory, multiple plotlines, and her own romantic interest during the course of 4 seasons and 40 episodes.

Dear White People the TV series gave Black people and critics even more of a chance to faithfully indulge in the show. The series was able to dive into so much more as it continued its commentary on racial issues in America, with Ashley’s character being in the middle of all of it. There’s one plotline in season 1 that involves her helping rally campus support against the school police and ultimately getting a problematic 911 call released to the public, which becomes the impetus for change within the Black Students Union. That sparked all kinds of reaction and chatter online, and it was just one of many scenarios that played out that drove lots of conversation amongst Black viewers throughout the course of its run.

The cliche thing to do is to call Ashely Blaine Featherson’s role in Dear White People her breakout role, and by definition, I won’t argue with that. However, even though she was incredible in the film and in the series, I still think there is so much more to come from this amazing Black actress. And we’ve been fortunate enough to get just a little taste.

Ashley Blaine Featherson: Movies and TV Shows

During her reign as Joelle on Dear White People, Ashley would have the opportunity to procure guest roles on Mann and Wife, The Number: The Reboot, and Leimert Park, a Sundance selected web series that would eventually be acquired by BET. She also teamed up with director/producer Justin Simien once again, starring in Bad Hair, a comedy horror flick that included co-stars Jay Pharoah, Laverne Cox, Usher, Vanessa Williams, and Kelly Rowland—to name a few.

And once Dear White People aired its fourth and final season in 2021, Ashley would score another guest role in Grand Crew, as well as on Run the World, both of which were unfortunately cancelled after the seasons in which she appeared.

Acting wise, I don’t know what’s next for Ashley. There’s nothing in the upcoming section of her IMDb page, and I can’t find much of anything hinting at another role online. Either way, given her diverse filmography, which includes the dramatic nature of her role in Dear White People to displaying her comedic chops in Grand Crew, it’s safe to say that the acting world is her oyster and she is bound to have a number of opportunities come her way. That being said, as a Black actress, and given all that we’ve learned about Taraji P. Henson as of late, we certainly can’t assume a longtime sexist, racist and colorist Hollywood is doing right by her. But I have faith—in her no less. I also have faith in her ability to choose projects, whether it’s a Black TV show or something for the masses, as she has clearly stayed away from doing just any old sitcom or movie. Her first web series didn’t have to be the deep, authentic, carefully-written masterpiece that Hello Cupid was. It could’ve been some slapstick comedy that was all about viral laughs and cameos from Hollywood names. But it wasn’t. It was more meaningful, and quite frankly, better than that. And so that leaves me excited about whatever is next for Ashley Blaine Featherson, because we can trust that whatever it is, it’s going to be a project worth watching.

Ashley Blaine Featherson-Jenkins: The “Trials to Triumphs” Podcast

There are a lot of podcasts out there. Like a lot. And the numbers aren’t so much smaller for Black podcasts either. That makes it really hard to find a really good Black podcast worth listening to.

But look no further, because Mrs. Featherson-Jenkins has you covered with her (relatively) new podcast with The Own Network, “Trials to Triumphs”. In an interview, she says she wanted this podcast to provide a genuine, unscripted look at the challenges people face and the victories that come on the other side. She’s truly an amazing podcast host. Not only does she do an incredible job of sharing her own personal and professional stories, but she’s able to connect with her audience while doing so, all while being a rising Hollywood star. On her podcast she has featured the likes of Kelly Rowland, Necole Kane, Robin Thede, Michelle Williams, Danielle Brooks, Samara Joy and Laila Ali—a depth and range of Black woman unlike almost any other podcast out there. And to top it all off, the podcast is fan favorite, with a Listen Notes score of 45, which puts it in the top 1% of podcasts.

Ashley Blaine Featherson-Jenkins: What’s Next?

As mentioned before, we don’t know what’s next for the actor, producer, writer and now podcast host. In the interview with HuffPost, it was clear that whatever she’s doing next, she’s not putting any limitations on her opportunities. She appears to be ready for growth, no matter where it takes her, and while she admites to having certain aspirations, she wants to be open to opportunities that may be even greater than what she’s imagined for herself.

That just may mean she’s not fixated on acting alone. The podcast, of course, is proof of that. I, for one, just hope she continues to embrace what’s unique about her. As a Black, female, dark-skinned woman with natural hair, she has just about broken the mold on what a career can look like. Yes, there were many before her that paved the way, and there are certainly more that have made more money, created more projects, and sold more tickets. But there’s something to be said for an actress truly took what was special about the way she thought, the way she looked, and the way she saw the world carving a path of her own and being rewarded for it, not necessarily by the system, but by her other Black contemporaries. She then took that platform, created by her and shared with others, to new heights, starring on the biggest platform on the world and then partnering with greatest female personality in the world to expand her very own line of thinking and mission.

So given all that, whatever is next for Ashley Blaine Featherson-Jenkins, I’m here for it. I’m hoping she can become everything she aspires to be, and then some, and we at BlackOakTV will be watching her every move, because that’s what we do with all the Black folks we are assured are going to be great and leave a lasting and differentiated legacy.