Naomi Weisman is a Canadian-Australian and mother of three who loves to ramble with her dog, cook for family and friends, and laugh whenever possible.
I’ve always been a huge fan of comedy, particularly Saturday Night Live. So many iconic comedians have launched their careers from that stage, and Will Ferrell is definitely one of them. Over the years, he’s starred in some raunchy, decidedly un-woke films, which piqued my curiosity about this documentary.
For many of us raised in an era where the transgender experience wasn’t widely understood, the learning curve has been significant. Most people I know strive to be inclusive and are eager to learn about the transgender community, even if they come from different backgrounds with limited exposure to this evolving segment of society.
A decade ago, I didn’t personally know anyone who identified as trans, so the concept felt somewhat abstract. Now, however, I have friends whose children are part of that community, embracing their true selves by changing their names, appearances, surgical procedures, and pronouns. I have to admit that I sometimes stumble over pronouns and worry that I come across as disrespectful when that happens.
Will and Harper is a documentary that introduces us to the long-standing friendship between Will Ferrell and Harper Steele, a writer from SNL formerly known as Andrew Steele. When Will learns that his close friend of 30 years is coming out as a trans woman, they decide to embark on a cross-country road trip to process this new stage of their relationship—a heartfelt exploration of friendship and transition.
This documentary prompted me to reflect on the immense courage it takes to transition, not only in recognizing the need to live authentically but also in stepping out into the world and asking people to accept and love you as you are.
Early in their journey, Harper shares her fear of experiencing things she once took for granted as a man while traveling on road trips, like enjoying a beer in a dive bar or attending a sporting event. Honestly, I hadn’t fully considered this aspect of “coming out.” Given the current discourse surrounding trans people in various parts of the world, it’s understandable that her safety wouldn’t be guaranteed.
Throughout their 16-day road trip, Will and Harper encounter a range of reactions from old friends and strangers alike, many of which were incredibly emotional to witness. While it was disheartening to see some mean-spirited behavior directed at Harper—a soft-spoken and gentle person—it was equally moving to observe the impact this negativity had on Will.
Ultimately, this story is precisely what many aging Boomers and Gen X-ers need to help them understand the transgender experience. By sharing such an intimate part of their journey through waters many of us may never navigate, I feel I’ve gained a deeper, more sympathetic understanding of the necessity of living authentically.
In today’s climate, it’s crucial to discuss trans people and their rights to live freely, safely, and happily. We need more love and acceptance in our world, and this film beautifully illustrates just how powerful that can be. Bravo to Will Ferrell and Harper Steele for their courage and openness in sharing this vital story!
P.S. Don’t forget to listen to the song at the end. It’s written and performed by a former cast-mate of Will’s on SNL named Kristen Wiig, Harper and Will Go West. It made me cry! A friend is a friend is a friend…til the end
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