Kelly Oxford can do anything, it seems: She’s a bestselling author, a social media star, and a newly minted filmmaker. The Canadian native first caught the world’s attention with her funny and confessional Twitter account, which eventually led to a book deal (the 2013 hit essay collection “Everything Is Perfect When You’re a Liar,” followed by 2017’s “When You Find Out the World Is Against You: And Other Funny Memories About Awful Moments”) and multiple optioned scripts that drew the attentions of everyone from Drew Barrymore and Jessica Alba to Diablo Cody and Cameron Crowe.
And she did it all while managing an anxiety disorder she was diagnosed with at the tender age of 19. As a 43-year-old single mother of three, Oxford still has to deal with those feelings — she’s the first one to tell you they never just go away — but now she’s harnessed them to craft her directorial debut, “Pink Skies Ahead,” which debuts October 18 at AFI FEST.
The charming and insightful ’90s-set coming-of-age dramedy stars Jessica Barden as Winona who, just as Oxford did in suburban Calgary, struggles with an anxiety disorder after dropping out of college and moving back in with her parents. (Another inspiration for the film beyond her own life: “Ghost World.”) The film’s supporting cast includes rising stars Rosa Salazar, Odeya Rush, Lewis Pullman, and Devon Bostick, in addition to household names like Michael McKean, Marcia Gay Harden, Henry Winkler, and Mary J. Blige.
“Pink Skies Ahead” got its start as an essay that chronicles Oxford’s own diagnosis, “No Real Danger,” which appeared in “When You Find Out the World Is Against You.” It was, fittingly enough, a moment of fresh anxiety that pushed Oxford to turn it into a script, just as she was grappling with the fallout of her 2016 divorce and trying to determine what was next for both her family and her career.
“It was a moment of pure devastation and anxiety, where I was just like, ‘Do I have to move back to Canada with my three children?,'” Oxford recalled in a recent interview with IndieWire. “Being a single-family income is very stressful, and I was just like, ‘What am I going to do? How am I going to keep living like this? What is the next thing I’m going to write?’ It was a rock-bottom stress moment, and sometimes things become crystal clear when you’re thinking like that.”
That thinking pushed her into one actionable direction: Make something that would help people who felt just like she did. “I was like, ‘Oh, my God, that’s it,’ that’s a story that helped people on paper,” she said. “Of course, it’s going to do the same thing in film. I spent five or six days just not sleeping and writing the first draft of the script, and I felt immensely better when I finished it.”
Some of her story’s details changed in the script — the location moved to her adopted home of Los Angeles, all the better for down-home indie filmmaking — and Oxford said it was helpful to find a way to rewrite her own narrative. “I definitely wrote a bunch of plot that absolutely never happened,” she said. “But I made sure that it was synchronistic to what had actually happened in my life, the way I avoided my diagnosis, how I busied my time with things that sort of weren’t important and weren’t helping me just to avoid my anxiety.”
Oxford was clear from the start that she wanted to direct the film, although she’s spent enough time in Hollywood to know that’s not always possible. She’s sold plenty of scripts, both for films and television, none of which had been made before “Pink Skies Ahead.” “Oh, my God, so many scripts,” she said with a laugh. “So many.”
When I was 19, working as a waitress, a woman came in with her 10yo daughter “No meat, no dairy, no wheat, no nuts, she’s deathly allergic.”
Without thinking, I said, “Why are you eating in a restaurant?”
I was not fired but I think I should have been.
— kelly oxford (@kellyoxford) July 29, 2020
Funnily enough, it was one of those stalled projects that helped make “Pink Skies Ahead” a reality. In 2012, Warner Bros. bought “Son of a Bitch,” one of Oxford’s earliest spec scripts, which chronicles a young party gal who discovers she’s pregnant and has to deal with what’s next. Then-Warners president of production Greg Silverman made that deal; in 2017, he founded indie producing outfit Stampede Ventures. Two years later, Silverman set “Pink Skies Ahead” as the label’s first feature.
“It was surreal, for sure, and it felt right,” Oxford said. “It felt like this was supposed to be the time that I directed my first movie, and it absolutely should have been this movie. So I’m really happy with everything, the way it all came out. Even with all those dead scripts out there, this was really the first one that I was supposed to direct.”
For her on-screen surrogate, Oxford cast “End of the Fucking World” star Jessica Barden, whom the filmmaker terms a “little powerhouse.” Thank social media for that connection, too: When Oxford started casting, she was pleased to see that Barden followed her on Instagram, indicating she at least had some sense of her and her work. When the duo first met in person, Barden admitted she’d also read Oxford’s books. “She really did know who I was, and I was like, ‘Oh, this is great. You like me,'” Oxford said. Which meant, of course, that Barden also liked Winona.
Oxford shot the film in Los Angeles last summer, where she tried to shape a positive experience for everyone involved, all the better to alleviate any anxieties. “I think the responsibility to the cast and crew was a lot heavier than I expected, but that’s just on me, that’s just the way I am,” Oxford said. “There were no hangups, there were no problems, there were no interpersonal issues. I just felt every day that I had to make sure that the environment was really great for everybody. I’m very hard on myself, and I take things very seriously. I mean, I’m a mom. Being on set was like multitasking heaven to me.”
Pre-pandemic, “Pink Skies Ahead” was expected to debut at SXSW this past March. When the festival was cancelled, Oxford responded in characteristic fashion. In an Instagram post announcing that the film’s world premiere was on indefinite hold, Oxford telegraphed both her joy in its SXSW selection and her devastation that it wasn’t happening.
“The first week [after the cancellation], I was just lost,” Oxford said. “I felt so bad for people that had bought tickets and were excited for it to come out. I felt lost in knowing what to tell everybody that wanted to see it, especially the people, obviously the people that want to see it because they relate to it. I thought, ‘That’s a great thing to dangle in front of people’s faces and then take it away from them!'”
Eight months later, “Pink Skies Ahead” found its premiere home at AFI FEST, which will host a virtual premiere this weekend that includes a post-screening chat with Oxford and Barden. She’s cagey on sharing next steps for the film, but said she is “very optimistic about the future for it.” (After the publication of this interview, MTV Studios picked up the film.)
“I just hope that people feel less alone when they see the story in their own anxiety,” Oxford said. “There’s so much uncertainty in being young and in a transitional period of your life, but that happens over and over throughout your life as you get older. It happened to me when I decided to write this movie. I was uncertain, and I was in a transitional period, and I think that those moments in your life always make for great films.”
Oxford’s transitional period isn’t over just yet. Remember “Son of a Bitch”? Eight years after selling it to Warner Bros., Oxford will finally get to make it with Silverman, who (along with Stampede and Kerry Roberts) is producing the film for HBO Max. In July, Oxford locked in her deal to direct the feature, which is casting now.
“I’ll take it all. I’ll take as much as I can work on,” she said. “I love working, and I have to work, because I’m alone with three teenagers in Los Angeles.” She added with a laugh, “Somebody send me a lifeline!” For many people, Oxford and “Pink Skies Ahead” will do just that.
“Pink Skies Ahead” will premiere at the 2020 AFI FEST Film Festival in the Special Presentations section. MTV Studios purchased the film in advance of its premiere and will debut it next year.