Former President Donald Trump won re-election in 2024. Part of his campaign included ads and commercials in swing states that were against transgender rights. Since President Joe Biden's election in 2020, Republican legislatures have introduced or passed tons of bills that have also been against transgender rights and even healthcare. Organizations like HRC and the ACLU have noted a record-number of anti-trans bills in the works. Therefore, this film, which is about a transgender woman and her celebrity friend, came at an opportune time before the election and remains a relevant one.
Harper Steele is a writer who most notably worked for Saturday Night Live from 1995 to 2008, even rising to the title of head writer and winning an Emmy Award. Harper was assigned male at birth in 1961. However, in 2022, at the age of 61, Harper decided to transition to female fully. She had to come out to her family and friends. She did so by writing letters to everyone. One of the letters was sent to Will Ferrell, the famous comedic actor who started on SNL the same year as Harper and who has since become one of the biggest Hollywood stars.
Will decided to take Harper on a cross-country, road trip, going 3000 miles, driving from New York City to Los Angeles, making stops in what's considered red states, conservative areas or Trump country. There wasn't a political angle to Will's decision. Harper had grown up in a red state, that of Iowa, and had a practice of doing solo, road trips to those aforementioned areas, but those trips were when she identified as a man. Ostensibly, the trip would be to acclimate Harper to those same places but now as her new identity of being a woman.
Essentially, she achieves that to some degree. Yet, the question becomes what is the difference between Harper entering those spaces as a man as opposed to entering as a woman. She talks about going into truck stops or biker bars as a man, but she never clarifies what the difference is in the fundamental experience. There's a scene here of her going into a biker bar that has a Confederate flag hanging inside and an anti-Biden sign sitting on the ground. However, when Harper was a man, did she confront the people there on their politics? She announces to some people that she's transgender, but she does so in a way that seems as if it's for no reason other than gauging their reactions. It's never clear if she would gauge people in those spaces on political issues prior to transitioning. Would she gauge them on the Confederate flag brazenly flying overhead or the anti-Biden sign in the corner?
Harper never experiences any transphobia in person. After several stops in restaurants or bars, there's this suggestion that maybe the transphobia that Harper feels is internal. We don't see any transphobia that's external or at least face-to-face, if you discount the occasional misgendering. This film almost stands as wanting to make liberal-minded people not pre-judge people in those rural or red-state areas because they might not be as bigoted or discriminatory as one might fear. However, we do see a lot of transphobia thrown at Will Ferrell for being friends with Harper online via social media. The presence of a film camera documenting Harper might have shielded her from any face-to-face transphobia. If people know they're on camera, they might be on their best behavior.
Other times, Will's celebrity was another kind of shield, which Harper does acknowledge. One example is when Will and Harper attend a NBA game in Indianapolis. They meet the Governor of Indiana, Eric Holcomb, a Republican who has supported anti-trans bills in his state. Yet, when Holcomb is with Will and Harper, he's all smiles and pleasantries. In their defense, Will and Harper didn't realize Holcomb was the governor. Afterward, Will suggests if he had known, he would've confronted the governor about his beliefs or thoughts about trans people. This is fine, but the documentary never attempts to do any kind of confrontation with anyone who might have those some right-wing or conservative politics after the incident with the governor. The scene with the governor happens early in their 16-day trip, so they had plenty of opportunities, if they wanted.
Yet, it underscores that this film isn't a political piece. Despite moments where Will Ferrell will dress up and play characters in public, this film isn't Borat (2016). Will's goal isn't to confront people and expose them in some satirical way like Sacha Baron Cohen did. Will is just trying to be a goofball. If anything, the transgender stuff is incidental. This film is really about demonstrating how great a friendship Harper and Will have and it's particularly hagiographic about how great a friend Will Ferrell is.
The real great moments though are moments when Harper is relating her true feelings about her experiences. Through her, we get a heartbreaking account of being a closeted transgender woman. There is a moment when they talk to another transgender woman in Peoria, Illinois, named Dana Garber. Dana relates issues with transitioning later in life and how misgendering often results from her voice being so deep. Hearing from trans people like Dana about their authentic experiences is gold. Unfortunately, this film doesn't have enough of stories with people like Dana. Instead, this film is stuffed with Will's comedic bits while he attempts to be funny like when he puts on a costume at a Las Vegas dinner.
Will is technically there to be an audience surrogate and ask questions to his friend that most people might not get to ask. However, it's clear that Will isn't a great interviewer and often fumbles when asking obvious questions about top surgery versus bottom surgery. Yes, he doesn't want to be offensive or hurtful to his friend, but it doesn't make their interactions all that engaging. Harper just ends up doing a lot of the heavy lifting herself, making Will's presence at all feel almost unnecessary.
Finally, the song in the end credits is a track called "Harper and Will Go West." The two talk about making a song for the documentary and they ask Kristen Wiig, another former SNL cast member to create one. The film teases the possibility that she's not going to be able to do it. Spoiler alert she does and it should definitely be up for Best Original Song at the upcoming 97th Academy Awards.
Rated R for language.
Running Time: 1 hr. and 54 mins.
Available on Netflix.