We chat to Ashlei Sharpe Chestnut, an up-and-coming actor and star in Cruel Summer on Amazon Prime Video and Freeform

Ashlei Sharpe Chestnut recently played Ashley Wallis in Freeform’s new psychological drama, Cruel Summer.  If you have yet to watch it I recommend you stop reading now because there will be spoilers. As a fan of the show, I jumped at the chance to interview Ashlei about the show and what season 2 could possibly look like. 

We also talked about her upcoming projects, like her upcoming show Rap Sh*t which was written and produced by Issa Rae. Ashlei was a delight to talk to and I’m looking forward to seeing what she does next! 

MR: You were recently in Freeforms Cruel Summer, (which was absolutely brilliant by the way). What was it like navigating that role, with all its twists and turns?

ASC: I felt at ease with Ashley’s character. Even though we were bouncing back between years, I think because she had such a shift from curtness to remorse, there was a clear delineation between emotions and Ashley’s state of mind.

MR: In the finale, it was revealed that Jeanette was guilty all along. How did you keep such a huge secret and did it blow your mind once it was revealed to you?

ASC: Fun fact! A lot of us didn’t know how the series was going to end, we were watching live with the rest of the world when that last clip of Jeanette aired. I was shocked! But also relieved because I was very vocal about being #TeamKate all season. 

MR: There were so many moments where I felt she was guilty for sure but I did doubt myself after the snowglobe episode where we find out that it was Mallory and not Jeanette on the bike. Did you doubt Jeanette’s guilt after that episode aired?

ASC: There were moments for sure where I was a little sympathetic towards Jeanette, and began to question Mallory’s motives. But no, I never thought she was completely innocent because Jeanette had way more to lose if Kate returned. If Kate stayed in the basement, Jeanette would still be this popular girl, ya know?

MR: For sure! 

MR: Cruel Summer will be returning for a second season! What are your hopes for your character next season? 

ASC: First let me say, I was super surprised at how much audiences loved Ashley’s character. I would hope that Ashley’s storyline continues to flesh out. I want her to have that moment to check Derek for breaking her trust and to expound on her growing relationship with Kate after it’s revealed Ashley’s the one talking to her in the chatroom.

MR: OMG yes! I was so pissed off when Derek betrayed you and I was waiting for you to have your moment to unpack that, I really hope you get your chance next season. I think it was easy to fall for your character because we saw someone who I feel was dealing with really relatable issues. Your character grew and although it was initially driven by your guilt and remorse you were able to build a genuine relationship with Kate and show a different side to your character.  

ASC: I’m happy that her shift came across to audiences. I know after episode 4, people online were questioning her motives. They didn’t know if she was really trying to rebuild that relationship with Kate, or if she was trying to get back at Kate by trying to help Jeanette because she was seeing Derek. There were so many fan theories that made me laugh.

MR: No way, I totally thought you made it pretty clear where your intentions lay. 

MR: I’m hoping you get more screen time, I feel like Ashley has a few secrets of her own. 

ASC: Oh, she definitely does!

MR: Do you know whether or not the next season will be filmed in the '90s again or will we be visiting a new decade?

ASC: I have no idea.

MR: What would be your dream decade to visit or revisit? Mine would be the 20's, 50's and 80's. (but without the heavy racism)

ASC: I like how you added the “without the heavy racism” because I was getting ready to say, I’ll just stick to the present hahaha! But sans racism, I would definitely visit the 70s & 80s. The music from that time period stays on repeat. And the parties were insane! You could do whatever and not have to worry about it showing up on someone’s Insta Stories the next day. 

MR: You’re like this mysterious person that is threaded throughout the main storyline, coming in and out and I would love it if next season your story has more of a focus. I’d also love to see more of Vince and Ben's budding relationship. 

ASC: Same here!

MR: Also, congratulations! You were recently cast in Issa Rae’s new HBOMax show Rap Sh*t, can you tell us a little bit about the show? 

ASC: I’m THRILLED about this show! Being able to work with Issa Rae has been on my bucket list for a while now. I can’t go too much into detail, but the series follows two estranged friends, Shawna and Mia, who reunite to form a Rap Group. And my character Fatima is a law student that’s really good friends with Shawna’s boyfriend Cliff. That’s so vague haha! But I’ll give you a little something extra and say that some of the names I’m seeing on our call sheets so far are very exciting. 

MR: I absolutely adore Issa Rae and I am very excited to check this out. Sounds awesome. I'm hoping to have a reprise of her rap Broken Pussy. 

ASC: HAHAHA CLASSIC!

MR: What attracted you to this role? 

ASC: One, the fact that I’m a huge fan of Issa’s work, I’ve been following her career for over a decade. I remember sitting in my dorm room in college watching her YouTube series Awkward Black Girl. And two, this is Issa’s next scripted show that she is writing, and having watched Insecure these past few years, only made me want to join this production even more. 

MR: Yes! Awkward Black Girl was everything. 

ASC: Right?! Yeah I think that show was the first time, at least that I can recall, seeing a Black girl in a show that was awkward, and quirky and funny. I really resonated with that show.

MR: Issa Rae is a force of nature, what was it like to receive the call that you were going to be working with her?

ASC: I remember feeling really gleeful. I also had a feeling that they’d enjoy my audition because I played a Drake song during one of my takes haha!  I knew Issa loved Drake, so I feel like that’s partly what reeled the whole team into casting me- at least that’s what I’m telling myself.

MR: Are you looking forward to doing something a little lighter after doing Cruel Summer? 

ASC: Yes and no. I don’t mind the heaviness, maybe because I’m currently working on this comedy. I’m also working on another production- I can’t disclose what it is just yet, but there’s a balance that I’m really happy to have at the moment. I’m being able to play in different genres right now which is an actor’s dream.

MR: Do you have any plans to go back to Broadway?

ASC: I would LOVE to go back to Broadway! I’m itching to go back. My career started on the stage. I’m interested to see what musical or play will bring me back. I mean, even if it’s across the pond to The West End, I’d be super happy. But yes, I do plan to return.

MR: If you could pick a comeback role what would it be? I would love to be Velma Kelly in Chicago or Elphaba in Wicked. 

ASC: Oh man! A comeback role? I would- Okay pause, Velma Kelly is ICONIC! I was singing Cell Block Tango the other day. Elphaba is a good one too. Maybe Audrey from Little Shop of Horrors. I think I’ve got her belt down from Suddenly, Seymour. 

MR: OMG yes! I would also just love to somehow play Anita and Riff in West Side Story so I can do America, Cool AND Officer Krupke. I was so obsessed with those songs and the choreography as a kid. Jerome Robbins was everything, a visionary. 

ASC: A. Visionary. If I had better ankles I would’ve loved to try one of his ballet pieces too. 

MR: Representation is so important especially when it’s done correctly, what movies or shows have you watched recently where you have felt represented as a person?

ASC: Michaela Coel’s ‘I May Destroy You’, Issa’s ‘Insecure’, and a few other things. But personally, I want to name those two because I’m a writer as well, and being able to see these women not only star in and produce their projects, but also write them especially with such a huge platform, it’s awe-inspiring. 

MR: Michaela Coel and Issa Rae are two writers who are able to write about black women well. I feel like a lot of writers fail in this area because they are unable to individualise us and tend to use popular stereotypes like a clutch which immediately makes me lose interest. Black women are as individual and unique as white women, and I feel like people fail to create whole characters when writing black characters - we aren't all into Rap, we don't all sound the same and we all have very different upbringings so it is important for this to be reflected on screen. I rarely ever connect or see myself represented as a black woman on screen but I do in the works created by Michaela and Issa. In the last couple of years, things have improved and we have been blessed with well rounded black characters like Simone from The Good Place, (although Kirby Howell-Baptiste is brilliant in everything), Robyn in High Fidelity, Analise in HTGAWM and Dr Brook from In Treatment. I remember when there was a time where I couldn't even pick 5 black female characters that were relatable and I felt represented me in any way. 

ASC: Absolutely, I keep hearing folks talk about the new Black Renaissance that is happening right now which is so funny, because literally one hundred years ago was the Harlem Renaissance where we had that influx of Black art take over. And they too were just getting over a pandemic. I just feel blessed to even be living at this moment and creating during this time. 

MR: I look forward to one day seeing your work, do you have anything in the works at the moment? 

ASC: I do! I have a couple of scripts that I’m working on getting into production hopefully within the next year. When we chat again, I’ll give you an update!

MR: Yes please, I look forward to it!

MR: What would be your dream role and why?

ASC: It’s still Marvel’s Ororo Munroe AKA Storm. But also starring in roles that I’ve written with adequate funding and with a bigger platform, would be a dream.

MR: You were due to star in Kevin Costner's National Parks until ABC hit pause, do you have an update about the future of the show?

ASC: Yeah, surprisingly the show didn’t get picked up. Not sure if they’re shopping it to other networks, but for now it’s not moving forward.

MR: I love the fact that you told your mum that you wanted to be inside the TV after watching an episode of Barney and Friends. Do you see yourself ever getting behind the camera one day? 

ASC: Other than writing and producing? I’m not sure… I mean, never say never. I’m sure eventually down the road I’ll want to direct something, but at the moment my focus is more so on writing and acting.

MR: Name three things you can’t do without?

ASC: Aside from family/love and all the sentimental stuff I’ll say: 

Music, a baseball cap, and a good pair of fun socks.

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