I was not expecting a Will Ferrell movie to teach me about allyship

I’ve been a fan of Will Ferrell for as long as I can remember, and I don’t think this is a particularly unique experience. 

The comedian has been making the world laugh since the 90s, from his SNL sketches to his ridiculous movie roles and outrageous interviews.

When I heard that he was releasing a documentary, I was keen (who wouldn’t be?), and after I watched the trailer, I was completely taken aback upon learning the subject matter.

Will Ferrell certainly isn’t the first name I would associate with a film about the trans experience. I think that’s what made me instantly curious. How would a man known for his outlandish and very bro-centric sense of humour handle such a delicate topic? And should we even be entrusting a cis straight man to be at the helm of this film? 

While I grappled with it, I eventually decided that this might be Will & Harper’s secret weapon. Will brings to the table an audience of die-hard comedy fans who are unlikely to seek out a film like this, but perhaps their beloved funny-man can act as the trojan horse; opening the minds of those who prefer their films to be less complex and, whether consciously or not, push against progression.

During the pandemic, Will received an email from an old friend and colleague, known then as Andrew Steele. The two were coincidentally hired in the same week (Andrew as a writer) on SNL back in the 90s and grew closer over the years both personally and professionally. 

“Hey Will. Something I need you to know. I’m old now, and, as ridiculous and unnecessary as it may seem to report, I’ll be transitioning to live as a woman,” Will reads the email aloud.

“In the last ten years, I’ve been trying to understand what’s going on. Tried to get rid of it over and over again throughout my life. Now I’m giving up the fight,” continues Harper, as we see her on screen for the first time. “I doubt being a trans woman will change my personality that much. Instead of an asshole, I’ll be a bitch.”

This is the first time I’m distinctly aware of how this movie will be treated: With honesty, openness and humour. 

The two continue reading the email back and forth. It’s beautiful and revealing, and at the crux of it, it’s one friend reaching out to another, signalling for support. 

“The biggest question when people come out of the closet is, ‘Will I still be loved?’. I’ve met trans people who were not loved when they came out. I don’t doubt that Will is my friend, but I’m not Andrew Steele anymore,” Harper reflects.

“Okay, where do we go from here?” Will asks the camera. 

Where the pair go next is a two-week road trip across America. “I love this country so much, I just don’t know if it loves me back right now,” Harper reveals, which is a completely fair yet heartbreaking sentiment.

The idea is for Will and Harper to establish a new dynamic of their friendship, whilst simultaneously visiting different cities (with widely different political views) along the way. The pair have a lot of questions for each other, and what is established very early on is that they’ve fostered a completely safe space for each other. 

Will is aware of his privilege (not only being a rich, famous movie star but simply a white, straight male), and admits to some nerves around asking questions. You can tell he really wants to navigate this tactfully, but in a way that feels true to their decades-long relationship. There are poignant questions and discussions, followed seamlessly with jokes that feel authentic to the pair. The two are both aware of Harper’s safety, and while Harper chooses to navigate certain spaces solo, she has Will on speed-dial, ready to call him in to diffuse any situation that goes awry. 

The trip starts in New York, including a lunch with Harper and Will’s SNL alum, Tiny Fey, Tim Meadows, Seth Meyers and writer Paula Pell. The group embrace Harper instantly, as do the other famous funny faces we see along the way (Kristen Wiig, Will Forte, and Molly Shannon). We also meet Harper’s sister and her kids. They all support Harper and share their experiences with Will and the cameras.  

Harper grapples with the places she once visited with ease, predominantly middle-America. It’s fascinating and frustrating watching the interactions these two have with strangers, but I’m in awe of how Harper in particular carries herself. She firmly but kindly corrects the people they encounter who consistently misgender her. More often than not, people seem apologetic for doing so, but you can’t help but wonder how these interactions might go down sans camera-crew and adjacent movie star.

Will does his best. He proudly introduces Harper and openly shares her recent transition, but as the trip progresses, he reflects upon how to effectively be an ally for his friend. When they go to an NBA game in Indianapolis, they meet the Governor, Eric Holcomb. Will chats to Eric, explaining the project openly and the interaction seems friendly enough. When he sits down, Harper asks for the Governor’s name and they google him, discovering he is responsible for the passing of several dangerous transphobic bills. The next day, Will admits he dropped the ball, as he hadn’t anticipated the interaction. “I wish I’d had the wherewithal to be like, ‘What’s your stance on trans people?’” Will tells Harper as she drives. 

In one of the harder scenes to watch, Will and Harper go to a steakhouse in Texas, famous for its deal of a free 72-ounce steak if you can eat it in one hour. Will, being Will, decides to not only accept this challenge, but to do so in character. Harper arrives at the Steakhouse that night with Will fully in character as Sherlock Holmes. Instinctively, it’s funny. Will is completely absurd and he’s bringing levity and light to the restaurant. But given the reality of the situation, it backfires. The waiter who announces the pair for the competition initially stumbles upon introducing Harper as “miss”. What’s worse, the restaurant posts a picture of the two on their Instagram page and opens Harper up for a barrage of transphobic insults. 

The next day in the car, Will completely breaks down. “The saddest part for me is, uh, I just feel, I feel like I let you down in that moment. I was like, ‘Oh shit. We’ve gotta worry about Harper’s safety. You know?’” he cries, as Harper comforts him. 

Later when pulled over for a break from driving, Harper decides to read some of the tweets they’ve been receiving while on their trip. They’re all deplorable. Will is referred to as “a satanic illuminati paedophile”, and Harper’s existence is completely reduced. It leads to a very open discussion about the burden of trans hate, and Harper’s former suicidal ideation. 

Prior to Texas during a visit to Harper’s hometown in Iowa, the pair are pleasantly surprised with interactions at a local bar and the racetrack. There are some clunky interactions, but ultimately, the two are greeted with warmth. Still, it’s all incredibly overwhelming for Harper. “I’m a little bit in shock, and that’s not on them, that’s on me. I’m not really afraid of these people, I’m afraid of hating myself,” she admits to Will after sharing her story with some kind locals at the track.  

“Whoa,” Will responds, which feels simple but carries weight. The two cry in the car. 

When arriving in Vegas, Harper decides that Will should take her out for a fancy dinner. 

 “Let’s dress up. I’m not gonna pull a Sherlock, but maybe this is an opportunity to have more of a normal experience,” Will tells her.  “It would make me feel good because I feel like I would be in another environment that I haven’t really been in,” Harper shares. They go shopping for fun clothes (and wigs, in Will’s case) to wear for their night. Heading into different shops, Will asks Harper if she’ll be okay without him, and it’s nice to see his awareness growing. It’s not just dive bars and sporting games that Harper might not feel safe in, it’s also female-centric spaces. 

The two dress up (Will of course in ridiculous glasses, a wig and fake moustache), and share a lovely meal together. Harper reflects, “This whole trip, obviously, you’re taking the heat off me, and that’s just not the life of a real trans person. But when I was in the Goodwill today, I just felt way more comfortable and that’s a bit of a result of this trip.”  

Harper then shares with Will how complicated her feelings are towards her appearance. “Sometimes, the better my makeup looks, the worse I feel about my face.” Will tells her she looks great, but Harper continues. “There’s something about the slow process of getting used to who I am, that the ‘prettier’ I get, the more I see the flaws.” She tells him she’s more aware of her “unfortunately, very masculine face”.

“Having spent almost two weeks with you now, I’m just sort of like, I’m just with Harper. I’m forgetting the dead name, it’s just getting fully replaced, and I don’t… I don’t know.” Will tells Harper, who thanks him genuinely. “Do you feel lucky sitting across the table from someone who looks like this?” He asks Harper, pointing to his ridiculous moustache that keeps falling off his upper lip. No moment is too poignant to follow up with a joke, and it feels like that’s what makes their relationship so special.

The film and their road trip comes to a close, ending in the final destination of California. The two sit on the beach at sunset, feet in the sand with a cracked beer. After reflecting on the trip and the joy it brought them both, Will tells Harper he has a gift for her, and pulls out an aqua-blue box. 

“We’ve obviously had this back-and-forth on beauty, and being okay with kind of, you know… Whether it’s makeup or finding the right dress, making yourself feel good as a woman, beautiful. So, I thought to myself, ‘Oh I know what I wanna get Harper at the end of the thing, her own pair of diamond earrings’.” 

Harper cries instantly, (and so do I). 

“Just as kind of obviously a memory of the trip, but just like, it’s okay to feel pretty, and do nice, pretty things for yourself.

“It’s just so cool,” Harper sniffles, smiling, “It’s just so sweet. This is very special.” 

The movie ends with footage from the trip scored by a custom-made song from Kristen Wiig, as requested by Will and Harper. It’s wonderful. 

What I loved most about Will & Harper was how raw it felt. I completely underestimated Will Ferrell’s involvement, and if anything, I felt that his lovable, approachable nature added a gentleness to the film. He demonstrated that even when you’re well-intentioned and open-minded, you’re not always going to know the perfect thing to say. But, if you love and respect someone, and you’re willing to learn and listen, important conversations shouldn’t feel too overwhelming to navigate. 

Will & Harper has received a 99% score on Rotten Tomatoes (i.e very good), and reviews have echoed the sentiment that the most powerful aspect of this documentary is its depiction of the impact of true friendship (something that gender should not define). 

“Will & Harper portrays Steele at a moment when she’s trying to negotiate the path back into humanity. Partly this is a matter of learning to live with bars full of rowdy Donald Trump supporters, but it’s more fundamentally about finding safety around the friends and family who are trying to learn how to relate to her. It’s an important thing for the cisgender world to see, and Will & Harper does its best to portray it in a thoughtful and heartfelt manner,” writes trans-activist Veronica Esposito, in her review for The Guardian. 

“It’s a movie with its share of blindspots, but it’s an honest, valid attempt. I very much hope that those who watch this movie are ready to see it.”

I very much hope so, too.

Will & Harper is available to stream on Netflix. 

Written by Lil Friedmann. You can follow her at @lilfriedmann on socials.

Image credit: Netflix + Punkee