Feminista Is Watching This So You Don't Have To: Will and Harper

Will and Harper hit the road, but why did they choose a janky station wagon?

By Michelle B. Taylor

Each week I’ll be bringing you the only TV and film recaps you need to read, so stick with me and we’ll get through the fall season as a family!

I often joke that I studied Sociology in undergrad because it’s the discipline for nosy people who like minding other people’s business. “People watching” is what some folks call it to make being nosy as hell seem like a respectable hobby.

It is no surprise, then, that I love a good documentary. I appreciate a deep dive into a person’s life, or a moment in time that offers different insight and context. So when Will & Harper, the new Netflix documentary about two old friends taking a road trip, came onto my radar, I decided to check it out. Half the states in this country are enacting anti-trans/ LGBTQ+ legislation designed to erase trans people from society, so this film is timely and relevant and I’m glad they made it.

Will Farrell is arguably one of the funniest and most successful Saturday Night Live alums, and he owes his tenure on the show and a lot of his best work to Harper Steele, the former SNL head writer behind some of his best characters and sketches. We learn that Harper advocated for Will when he auditioned for SNL, which led to Lorne Michaels bringing him on. With a friendship spanning more than 25 years, theirs is a special, fruitful, and enduring relationship. During the pandemic, Harper shared with Will that she is transgender and that she has decided to live her truth and finally be herself. “My whole career, my whole life, I performed as a man named Andrew, that’s how I’ve always seen it,” she says when they visit 30 Rock, their old stomping grounds. I appreciated how she articulated that, and I imagine that others think similarly of their lives before transitioning.

Will and Harper are hilarious, and the film begins in a way that leads one to believe it might be a mockumentary. Will has jokes from the jump and one might be tempted to believe he won’t be taking this journey at all seriously. It’s endearing, then, to see him step back from being the funny guy in every situation and just be a present, supportive friend to Harper. The pair load up an old janky station wagon (why..??) and set out on a road trip that takes them to places like Washington, D.C., Albuquerque, New Mexico, and Amarillo, Texas where Harper gets to be “out” and about in the world, navigating it in her new body, with her new style, and with an entirely new perspective. In many ways, the road trip represents her journey towards personal freedom and we are all invited to share it with her.

There are moments in the film that highlight some of the experiences many transgender people go through when they invite us into their lives. For example, there is a bit of a clumsy scene when they meet with Harper’s children who share how her transition affected them. I say clumsy because Will has moments when he appears unsure of how to navigate certain conversations, so he overcompensates with humor and jokes that aren’t always appropriate. Her daughter didn’t seem to have any issues with Harper’s transition, while her son had some struggles. There is an important moment when the son says Harper, who remains “Dad” or “Pop” to them, was his only source of masculine influence, so the transition felt like a loss. 

Then there’s another scene when they’re meeting with other SNL alums, including Tim Meadows and Tina Fey, and it seems like it’s the first time they’ve shared space with Harper since her transition. A rather strained embrace between Harper and Lorne Michaels made me wonder, “What’s the tea?” There’s something going on there and it was written all over their body language. As Will and Harper map out their road trip plans with their former coworkers, the scene speaks to the nervousness people may experience when coming out to people they’ve known for so many years. Harper expresses her concern about being accepted and her fear that people won’t want to rock with her anymore. Thankfully, everyone seems to embrace her and there’s an outpouring of love.

From 30 Rock they head to Washington, D.C. and there is a funny bit about trying to see Joe Biden. Will says he can use his face to get in, but they’re blocked of course. This sets the tone for what becomes an ongoing theme--Will’s fame shields Harper from a lot due to his celebrity status. People are more interested in him which allows Harper a bit of cover. Will takes the spotlight off of her but that isn’t the typical experience of trans people and Harper acknowledges that. At the same time, Will’s celebrity brings attention that leads social media users to make tons of hateful, bigoted comments that Harper may not have had to endure were it not for the spotlight being on them. 

While in Texas, one of the most hostile states for trans people, they visit a steakhouse and Will takes a challenge to eat a 72-oz steak in an hour. Harper is nervous because everyone is watching and recording them. This is one of the first times she’s had that kind of attention on her. The filmmakers flash on screen some social media reactions to the two of them and it’s all vile anti-trans stuff. “I feel like I let you down in that moment,” Will reflects. “We have to worry about Harper’s safety,” he acknowledges as they scroll through the comments together. It is a moment where Will understands some of the weight of Harper’s transness, which she said she felt was on display in a way she’d not yet experienced.

Throughout the film, there are a lot of “How did that feel?” moments, which become a bit repetitive and make the conversations seem less organic and a bit scripted. It’s also possible that the editing contributed to the repetitiveness. Road trips offer the perfect opportunity for raw moments--my son and I have some of our best conversations in the car. But they’re driving around with a camera affixed to the hood of the old janky station wagon (again...why?? They’re rich!). They didn’t even use a dash-cam or something similar.

Towards the end of their journey, former SNL cast member Molly Shannon meets with them and asks them what was the best part of the trip. Will shares, “I had no idea the kind of despair Harper felt for so long.” The road trip seems to open his eyes and heart quite a bit. Harper says, simply, “Will loves me,” which ends up being one of the most beautiful moments in the film. 

The documentary was neither great nor bad. It was somewhere in the middle. I appreciate the film being made and commend Harper for inviting us into her world and sharing her story with us. More people need to see that even when you’re a Hollywood bigwig, you can grow, evolve, struggle, figure things out, and still long for things that seem out of reach.

Did you see the film? I’d love to hear your thoughts.