Matthew Turner | On 27, Sep 2024

Director: Josh Greenbaum
Cast: Will Ferrell, Harper Steele, Tina Fey, Seth Meyers, Kristin Wiig
Certificate: 15

Directed by Josh Greenbaum (Barb and Star Go To Vista Del Mar), this engaging and necessary road trip documentary centres on comedian Will Ferrell and his good friend, former Saturday Night Live writer Harper Steele, who has recently transitioned at the age of 61. With Harper worried about what her new life will be like as a woman, and whether it will impact her friendships, Ferrell suggests that they take a 16-day road trip across America, in order to process everything together.

The pair begin their trip in New York, home of Saturday Night Live, where Will and Harper both met on their first day, 30 years ago. As Ferrell points out in voiceover, if anyone was puzzled over some of his crazier film project decisions – such as doing an entire movie in Spanish, Casa de mi Padre – it’s probably because Harper was involved in the writing.

As the pair travel across the USA, Harper opens herself up to any questions Ferrell wants to ask, no matter how dumb, and the results are both touching and revealing. In addition, Harper has brought along old journals and photographs for the journey, and her remarkably frank writing reflects the pain and anguish she’d experienced before transitioning, including thoughts of suicide and self-isolation.

For his part, Ferrell proves an excellent friend, willing to listen and supportive at every turn. However, he’s not above making mistakes and owning up to them – one of the film’s most emotional scenes comes when Ferrell breaks down and cries in the car, after what was effectively a stunt (him wearing a Sherlock Holmes outfit to a steak-eating challenge in a Texas restaurant) backfires badly, leading to some hateful social media attention.

More importantly, Ferrell demonstrates exactly what it means to be a good ally, and the film is certain to prove inspirational in that respect, as well as being a vital piece of representation for anyone experiencing a late-life transition. In addition, the film offers a fascinating portrait of an evolving friendship, as the pair gently redefine the boundaries of their relationship in light of Harper’s transition.

The only issue with the film is that it’s slightly disingenuous in terms of the documentary itself, and how it came about – indeed, there’s no mention of it, and therefore we’re none the wiser as to whether the road trip was planned first and the idea to film it came later, or whether it was always meant to be filmed. Similarly, the camera crew never appear on screen and they’re never referred to, which maintains the intimacy of Will and Harper’s friendship, but also makes certain moments and conversations feel staged.

On top of that, the presence of the cameras is arguably counter-productive at times. At one point, Harper decides she wants to experience a scuzzy bar on her own and leaves Ferrell outside, aware that his celebrity attracts too much attention. However, she’s still being followed by a film crew, and it’s debatable whether she would have had quite the same surprisingly warm reception from the bar room patrons if the cameras hadn’t been there.

In short, this is both a fascinating portrait of friendship and allyship, as well as an important film in terms of trans representation, particularly with a mainstream audience. It also ends on a delightful pay-off to a very amusing running gag, whereby Will and Harper call Kristen Wiig early on and ask her to write them a theme tune, and then all their subsequent check-in calls go to voicemail.

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