About
Hi, I’m Jessie. Your eccentric friend.
I’m a comedian, creator, speaker, host, and professional enthusiast of being yourself.
I’ve spent my career making people laugh, telling stories, and finding creative ways to make everyday life a little more interesting.
Somewhere along the way, I discovered that my love of ridiculous outfits, oversized accessories, and unapologetic self-expression was about something much bigger than fashion.
It was about confidence. It was about learning to like yourself. And it was about realizing that life gets a whole lot more fun when you stop worrying about what everyone else thinks.
Today, I share that message with a community of over 1.5 million people across social media.
Through comedy, fashion, storytelling, and a healthy dose of eccentricity, I’m on a mission to make the world a little more joyful. And hopefully encourage a few more people to wear the outfit.
The story so far
The lore.
A curated career retrospective. Where the comedy came from, and what it turned into.
Comedy
Chosen as one of 100 female creators worldwide for YouTube’s Women in Comedy program. Over three years performing at the Upright Citizens Brigade. Headlined Caroline’s on Broadway and opened for Hannah Berner on tour. Series for Just for Laughs (It’s A Date!), Betches, Above Average and Comedy Central.
Writing & directing
Created and co‑wrote Under the Influence, Betches Media’s first long-form scripted series. Co-wrote Forgotten Animals. Directed female-driven brand video for Mastercard, Good Housekeeping, Who What Wear, Bumble, Verizon, Elmhurst and more, often doubling clients’ social following. Wrote for Stassi Schroeder, Hannah Berner, Taylor Strecker and Andrea Lopez.
See the brand work →Acting & performance
National commercials for Kohl’s, DirecTV, Stainmaster and LEGO. Best Comedic Actress at Miami Web Fest, Best Acting Duo at the Independent Shorts Awards, Best New York Film at Imagine This Women’s Film Festival. Appearances on Bravo.
Podcasts
Hosted Middle Children with Chris Burns and Happily Ever Heard Of It, the world’s first happy comedian’s field notes on joy. Weekly co-host on The Taylor Strecker Show.
Three things to watch first
Notable accomplishments
- Best Comedic ActressMiami Web Fest
- Best Acting DuoIndependent Shorts Awards
- Best US NarrativeSF Indie Short Film Festival 2019
- Best New York FilmImagine This Women’s Film Festival
- Official SelectionInternational New York Film Festival
Press
As seen in.
In this indie pilot from Jessie Jolles and Sarah Smallwood Parsons, a group of women in charge of a struggling nonprofit devoted to the wellbeing of unpopular animals take it upon themselves to throw a luncheon for homeless raccoons, with disastrous results. Evoking the colorful tone and joke-a-minute pace of the best of the sitcoms that emerged in the wake of 30 Rock, Jolles, Parsons, and director Alec Cohen lead an impressively deep roster of characters that each get showcase moments. The only reason not to click it is to avoid your inevitable craving for a whole season.
— Vulture
Astoria’s ‘Diva of style’ and Instagram sensation wows fans with fabulous, attention-grabbing looks.
— QNS, July 2026
Modern dating is hard. Fortunately, Jessie Jolles has a few tips to help you find that special someone as part of her series It’s A Date! with Just For Laughs.
— Funny or Die
