This article originally appeared in the Summer 2024 Champion Issue of Showstopper Magazine.
With a career as vibrant and diverse as the characters she portrays, Jennifer Michele De Winter’s number one goal is to create art, in any form. We sat down with her to discuss her journey from acting to modeling, and even writing, and how her commitment to creativity and storytelling remains her foundation. And how, amidst her busy career, Jennifer remains grounded, channeling her energy into philanthropic endeavors that uplift communities in need.
Telling Stories
Growing up, Jennifer’s love of movies was the catalyst for her career. “[It] made me realize I wanted to tell stories,” she expressed. And while she made her start in similar movies to those she fell in love with, she now looks for roles that take her outside of her comfort zone. “I loved doing children’s movies and children’s shows. Now, I look for a challenge. Certain roles are perfectly right for you, and it’s an amazing feeling when you naturally connect to a character. At the same time, the more a role challenges me, the more fun it is!”
“It’s always an amazing feeling to be recognized for doing anything well that you love.”
One of her more challenging roles was Britney on Just My Luck. “I remember there were a few scenes that they told me to improv, and I hadn’t every done improv on set before, only in class,” she revealed. “I was nervous but also enthusiastic about being able to say what I wanted as the character.” Her advice for working through challenging roles? “I think even if you are nervous, never let it stop you, just let it fuel you.”
Trying New Things
Jennifer isn’t just looking for difficult roles, but ones that also involve new elements that she hasn’t experienced before. “When I filmed Joey and Ella, I had never worked with CGI so much before,” she admitted. “The kangaroo was CGI-ed the whole movie, so it was a learning experience figuring out how to act with something that wasn’t there.” Jennifer also got experience working in prosthetic makeup for her role in 9-1-1. “I got to experience what it was like to act with blackened teeth and cuts and bruises and prosthetic makeup. It was different and a new experience. And I tried not to mess it up during lunch,” she laughed.
Writing Riley
Fueled by her newfound experience, Jennifer decided to branch out even further in the industry, and began writing. She began writing her first short film, Riley, inspired by her own experiences. “At the time, I was living a lot f the same things as the character,” she confessed. “I, too, was looking to fit in. And I usually get my inspiration from my life or things I’ve seen that in some way influence me.”
Riley went on to be nominated for four Young Artist Awards and even won Outstanding Writer! “I was very honored and excited,” she shared. “It is always an amazing feeling to be recognized for doing anything well that you love.” It just encouraged me to continue to pursue all the things I love—whether it be writing, directing, or acting. It’s all a part of storytelling and that’s where the magic is for me!”
Jennifer’s Work in Philanthropy
When Jennifer isn’t acting, modeling, writing, or playing polo, she’s helping those in need. “I believe giving back helps us as much as it helps others,” she explained. Like her multi-passionate work, Jennifer is inspired by all causes. From partnering with Skechers for the Friendship Pier Walk helping kids with diverse abilities to working with Claire’s for St. Jude and Big Sunday, collecting food for Food Forward, helping Project I am for Giving Tuesday, or working with Toys for Tots around the holidays, “they’ve all had a profound impact on [her].” “I have been blessed to get to work with so many people with such big hearts that care so much.”
Fashion and Modeling
Before Jennifer found her love of writing and acting, she was a model for the clothing brand Justice, sparking her love for fashion. “I think fashion also plays a big role in art,” Jennifer shared. “It’s a big form of expression.” Now, Jennifer has gone on to model for big names like Claire’s and Harper’s Bazaar—the latter another challenge for her. “I me the photographer at a modeling job I did years before,” she told us. “It was fun and colorful and we got to do it on Rodeo Drive. Since we shot outside, I was modeling in front of people walking by. I had never done that before, but people were nice and I think their positive energy added to the shoot.” No matter what the shoot is like, though, Jennifer is here for it! “I love it all. I think if we can create a vision together and deliver something that could work for myself and others, that’s wonderful.”
“Even if you are nervous, never let it stop you, just let if fuel you.”
Work-Life Balance
Jennifer isn’t just adventurous in her career, but also in her hobbies. “I ten to work hard, play hard,” she remarked. “It’s what I do. I can work really hard. But then when I have a day off, or just a few hours off, I don’t just like to rest, I like to do something fun, like boating or go out on the jet ski. [It’s a reward to myself for working hard. It really fills me up and gives me energy to get back to doing what I love most, telling stories.” Her favorite adventurous activity is riding horses and playing polo. “[It’s] such a thrill. So, whenever I can play, I go play.”
While it admittedly took time for Jennifer to find a work-life balance, she believes that finding a happy-medium has actually benefitted both her career and her personal life. “My hobbies all help me to be creative,” she concluded. “The more creative I am, the better I get at being creative. I get to express myself differently in each art form. And I love that.”
