Jessica Watkins

In 2014, New York-based, Tennessee-raised comedian Jessica Watkins walked from Delaware to California over the course of eight months in an effort to tap into her creativity while jump-starting her career. She filmed the entire journey to create her new film SPECIALish, a funny and enlightening documentary that is available digitally beginning on May 11, 2021. The film reveals how – throughout the trek – Watkins found herself connecting with nature, herself and humankind in ways that reshaped her relationship with her past and opened up her future.

SPECIALish is a film that I’ve been working on for seven years so I’m excited to share it with people especially after the last year that we’ve been through where we have spent a lot of time by ourselves. I think this is a cool story that will inspire people to think outside of the box and try something creative. I think it’s something that a lot of people can relate to right now emotionally,” said Watkins by phone earlier this month. “Also, it may give people some ideas about things we all want to do as we start to reopen the world and make some changes in our lives.”

At the beginning of the film, viewers find Watkins working at a restaurant and living with her partner and their adorable dog as she pursues her career in comedy. Inspired to push herself into new situations in stand-up and in life, she buys the right hiking shoes, learns to pitch a tent, and begins her journey. Later, we meet her mother, her sister and a cast of real-life characters who celebrate – and some who question – the call of the open road.

Jessica Watkins“I noticed that we all have so much in common. In general, people are good people and they want to help. We are mostly scared of what we don’t know. Some people have to stay in their kind of bubble because of fear,” said Watkins. “When I was on the walk, some people were so open and receptive. They were testing that with me by trusting in a stranger that is walking across America, letting me into their home and around their families even though they didn’t know me. It felt very communal. It made me feel really connected with community and that community not being specific to a place – since I was moving around – it was specific to a feeling. Ultimately, I think that we all have a lot more in common than we do differences.”

Watkins also found herself realizing previously unrecognized similarities between herself and her mother during a couple of visits to Tennessee as well as amid a leg of the journey in which her mother joined her on the adventure.

“We had to communicate because when I showed her the film at first she had some feelings about it. Ultimately I said, ‘Mom, I think that this is a story that a lot of mothers and daughters can relate to,’” Watkins explained. “It is authentic. That is my mom. That is totally the kind of relationship that we have. This has brought us closer together because we’re talking about real stuff so it helped us open up and communicate a little bit more. She’s seen the film a few times and she’s really proud of me.”

In between day-long treks pushing a stroller full of gear and spending nights camping, sleeping on stranger’s couches, or even pitching a tent on the side of the road, Watkins performed at comedy clubs and unconventional venues. Her jokes evolved as did her style – from planned out to a bit more improvisational – revealing how the journey was shaping her as a comedian and a person.

“It did change the way I think about myself because, especially when I was coming up doing stand-up, there was a lot of pressure to go up five nights a week. If you weren’t living in a shoebox with three other comedians and hated your life then you weren’t a comedian. If you had any friends or joy, you’re not a comedian,” Watkins said with a laugh adding that she now feels more freedom creatively. “I am an artist. Not just a comedian and not just a filmmaker, I enjoy creating. I want to make more films. I love comedy and adventure and I’m excited to keep exploring all those things as I move forward.”

One of the most authentic and compelling themes of the film is the perception of safety. As her well-being was constantly called into question by people in city after city, Watkins’ found herself coping with painful memories of a past sexual assault which occurred a decade earlier. This wasn’t an aspect of her life she was planning on sharing in SPECIALish, but as strangers continued to ask if it was safe for a woman to walk alone across the country – and one brash radio interviewer asked if she’d been raped or murdered yet – Watkins’ past was brought to the forefront of the conversation.

“It was not a part of the plan. Even in the editing process, it wasn’t always going to be a part of the film. Having that radio show recorded, that was the main catalyst for having it in the film,” said Watkins. “At some point when I was really getting into that story, once that was opened up, it did feel necessary for the story. It was real. It’s interesting that when I was in the walk, I didn’t really see it as the story that it is now. When I look at the footage, when I look at my writing, when I reflect back on how the film has played out, the walk was extremely cathartic for me. This is a new step of healing with this film for me. It’s awesome to be sharing my story because I feel like it’s a story that so many people can relate to – men and women – and not only do I feel really good about sharing the story, I want to encourage people to heal from their past traumas by opening up and creating art. And now that it’s in there, I couldn’t imagine the film any other way.”

The fact that SPECIALish is arriving at a time when we all just experienced our own year of relative solitude makes the film that much more rich and relatable. Rather than simply witnessing one-woman’s journey, the film feels like a grand odyssey proving anything – from growing closer to loved ones to discovering the joys of nature to starting a new career (or all of the above) – is possible.

SPECIALish is available all places digital starting today, May 11. Head over to to learn more about Watkins journey and keep up with her latest adventures on Twitter and Instagram at @ajessicawatkins.

(Featured photo by Mike Bryk)

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Laurie Fanelli

Laurie Fanelli is a Chicago-based writer and photographer who specializes in live entertainment coverage. She is at home at major music festivals like Coachella, Bonnaroo and, of course, Lollapalooza and...