Two Saturday Night Live alumni, actor Will Ferrell and writer Harper Steele, hit the road in the new Netflix documentary, Will & Harper.

More often than not, Netflix is in the news for not-funny transphobic comedy specials. Every now and then, they come through with an important documentary that makes up for their transphobic specials. I cannot tell you how many times I’ve written open letters to Ted Sarandos or called out the streaming service for another transphobic special. Frankly, the past few years have been exhausting with seeing the same thing over and over. This brings us to where we are today: Netflix is releasing a road-trip documentary featuring Will Ferrell and transgender comedy writer Harper Steele. While the film’s opening sees Ferrell deadname and misgender Steele, he’s become an ally for immediately correcting people. I can understand why Ferrell did this, especially with wanting to set up the film. Personally, I would not have done so.

Will Ferrell first met Harper Steele in the halls of 30 Rockefeller Center. It was Ferrell’s very first day after being hired for SNL. Suffice it to say, they have known each other for almost 30 years. As the world was going through the pandemic, Harper came out to Will through email as a transgender woman. The former SNL star was filming a movie with Ryan Reynolds at the time. You could imagine his reaction! Shortly thereafter, the two make plans to take a road trip together. The purpose of their trip is to process the new change to their friendship, let alone allow Harper to see the country as herself. They reexamine a number of things during their 16 days traveling the country together in early 2023. This film features less than 1% of the 200+ hours of film.

The road trips were easier for Harper prior to coming out. But traveling cross country post-coming out can lend to some uneasy feelings. Trust me, I can say from experience that I’ve experienced discomfort going through security at TSA because of being trans. The same goes for traveling to a state that has a negative attitude towards transgender rights. What if, G-d forbid, the wrong person see you walk into the women’s restroom and throws a fit? One of my worst experiences did not come in Texas but at Navy Pier in Chicago prior to a press screening. It was humiliating and awful to have a janitor knock on the stall door while I’m in the restroom. It might be nothing to the average cis person but I still have fear just walking into the restroom.

Will asks plenty of questions about being trans to Harper. Of course, there are the do’s and don’ts of what to ask or not ask. You never want to be too intrusive when it comes to trans people. During a conversation outside of Walmart, they talk about changes in their relationship. Will was worried about the ground rules. Would there be any changes? If Will loses any fans because of making this film, well, that’s just the trash taking themselves out because of their own bigotry.

Ferrell made news when they attended the Indiana Pacers-Philadelphia 76ers game on March 6, 2023–day 5 of their trip. Harper mentions that walking into bro-y cultures was one of the hardest part of her life. Having Will with her makes the experience less terrifying. He even met Indiana Governor Eric Holcomb on that Monday after the governor approached him. The governor had asked what brought them to Gainsbridge Fieldhouse. Will mentions that it is Harper’s first sporting event since her transition and the Pacers were nice enough to allow access. I would have immediately known going into the situation as to where Holcomb stood on transgender rights. They look him up during the game and later regret not addressing the topic. It would not even be a full month before Holcomb signed a bill banning gender-affirming medical care for minors.

Not surprisingly, a number of their former SNL colleagues join them at one point or another. Colin Jost is the show’s only current cast member to make an appearance. At one point, they call up Kristen Wiig to ask if she could write a theme song for their trip. While in Albuquerque, they go up in a hot air balloon with Will Forte. That’s the point where I would be freaking out!

I hope this film helps people. Excuse me while I get really personal here but where was this documentary when I needed it in the 90s?!? Coming out can be tough–not just for those of us who are trans but for the people in our lives. Mainly, the people that we have known the longest. Take it from me–sending emails and messages to many friends, family and rabbinic clergy were among the scariest things I’ve ever done and I’ve performed stand-up comedy on stage in front of both friends and strangers. A number of improv friends were among the first people I told. It is still terrifying to tell your friends even while knowing that comedian friends are generally liberal. I no longer talk to one of them for reasons that I’ve been extremely open about.

Coming out to family is by far the hardest, whether it’s through email, messages, and then seeing them post-transition. It can be terrifying. I had the OH, CRAP moment in November 2015 while living under the same roof as my parents! After moving, a few weeks repressing due to stress, and then starting hormones, I went full-time in late September 2023. This happened right as I got laid off as I was set to come out at a contract job. It got extremely ugly very quickly. I’m very open about my own story but I digress.

The film premiered this past January at Sundance before playing both Telluride and Toronto. Make no mistake that Will & Harper is one of the most important documentaries of the year–I wish I had this film when I was younger and not knowing why I had the thoughts and feelings that I did. Whether it gets an Oscar nomination or lands on the shortlist is up in the air. If it doesn’t make the shortlist, we’ll be hearing more about it during Emmy season unless the rules change again.

DIRECTOR: Josh Greenbaum
FEATURING: Will Ferrell, Harper Steele, Seth Meyers, Tina Fey, Kristen Wiig, Colin Jost, Will Forte, Molly Shannon, Tim Meadows, Paula Pell

Netflix released Will & Harper in theaters on September 13, 2024 and starts streaming September 27, 2024. Grade: 4.5/5

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