If you wanted to call Will Ferrell one of the greatest comedic voices of his generation, few would argue with you. From Saturday Night Live to his run of blockbuster hits, the funnyman has been cracking us up for the better part of the last 30 years.
But, as the old saying that goes, “behind every great man is a great woman,” and it’d be wrong to praise Ferrell without also giving flowers to Harper Steele, his long-time comedy partner and friend.
To be fair, Steele’s might not necessarily be a name you recognize yet, but she’s been the brains behind some of Ferrell’s most brilliantly batty work, ever since they first started working together on SNL in 1995.
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Will Ferrell as an Icelandic pop star in Eurovision Song Contest: The Story Of Fire Saga? Steele wrote that! Ferrell as a megalomaniac auteur in the sweeping melodrama parody The Spoils Of Babylon? Yup, that too! Ferrell and Kristen Wiig in deadly serious Lifetime movie A Deadly Adoption? Of course Steele was behind it!
Over their years of collaborating, Steele has pushed Ferrell to take some of his biggest and boldest comedic risks. But now she’s asking the actor to accompany her on the biggest and boldest journey of her life: Taking her first cross-country trip as an out trans woman and introducing the world to Harper Steele in her powerful new documentary, Will & Harper.
Born and raised in Iowa City in the ‘60s, Steele followed her lifelong passion for writing all the way to New York City, where she cut her teeth on scripts for the animated series Doug and MTV’s The Daily Show pre-cursor The Jon Stewart Show.
Eventually, those opportunities opened the door to SNL, where Steele worked for over 13 years, serving as co-head writer for her last four seasons alongside the likes of Tina Fey and Seth Meyers. Even though she formally said goodbye to the hallowed comedy institution in 2008, the connections she made there remained an important part of her life, both personally and professionally.
After decades of quietly struggling, it was just a few years ago that Steele, now in her 60s, wrote to a number of family and friends to share that she identifies as a transgender woman, was planning to transition, and would like to go by Harper.
Among the recipients was Ferrell, who was surprised yet immediately supportive. He had met trans people before, but didn’t know any personally, and had zero knowledge of the trans experience, which left him with one big question: What can I do to best support my friend in this new chapter of her life?
Before too long, the pair had hatched a plan: Steele, a longtime lover of road trips, wasn’t exactly comfortable doing one solo now that she was presenting as her authentic self, so Ferrell would ride alongside her, giving her a shoulder to lean on as the two made pit stops across America, having open, vulnerable conversations about transness and friendship along the way.
Soon, their life-changing trip—with every bump in the road—will be available for everyone to see in the documentary Will & Harper, directed by Barb And Star Go To Vista Del Mar filmmaker Josh Greebaum.
As you might expect, traveling anywhere with these two is a good time, and the film easily coasts off charm as they reconnect, share old memories, and poke fun at each other like only old friends can.
But Steele, in particular, keeps things grounded and candid, reminding us what’s at stake in this country, not just for her, but for the wider LGBTQ+ community. For every laugh, their journey also brings to light frank discussions about creating safe environments for trans people, the limitations of allyship, and Steele’s own privileges as a white, college-educated woman with a major celebrity at her side.
And therein lies the beauty of Will & Harper, too. After premiering at the Sundance Film Festival earlier this year, the doc was acquired by Netflix, where it’s due to premiere in the near future. With Ferrell’s star power on one of the largest streaming platforms in the world, there’s a very real chance audiences naive to or unfamiliar with the struggles of trans people will have their eyes opened by Steele’s journey, changing hearts and minds in the process.
“I should’ve made that decision [to transition] 40 years ago,” Steele tells Ferrell during one of the film’s most powerful scenes. “But I wouldn’t have had you guys. I wouldn’t have gotten hired [at SNL]. I would have had a completely different life.”
Among the many wisdoms gleaned from Steele in Will & Harper, the lesson that it’s never too late to live in your authenticity—and embracing every twist and turn in the road that got you to that point—is especially potent this Pride Season.
Here’s to many adventures ahead, Harper!
