Plodding with no illuminating moments.
‘Will Ferrell and his close friend, former head writer at SNL, Harper Steele embark on a cross-country road trip together after Harper comes out as a trans woman. Watch Will & Harper on September 27 on Netflix.‘
Built around the worn out conceit of the road trip, Will Ferrell and his Saturday Night Live pal, Harper (formerly Andrew) Steele, unpick how Steele’s ‘transition’ has affected their friendship. It’s a dull affair with some excruciating moments of ‘comedy’ from Ferrell, who seems more like a man who appreciates a sense of humour, rather than actually possessing one. We also have real product placement for Pringles (apparently they have a new smoky range) and Dunkin Donuts. Just shy of two hours, it is about three times the length it needs to be, for the meagre story it has to tell.
To set the scene, it’s after the pandemic, during which Steele had informed everyone that he was going to be ‘living as a woman’. We all know the drill by now, ‘living as a woman’ just means the dude grows his hair long, wears make-up and puts on a dress. Ferrell, sensing that he can create a narrative arc about his own kindness, endeavours to publicly indulge his friend of 30 years on this ego trip.
We have all the notes you’d expect to see, a shot of Steele’s bouncing high heel, supposed existential worries about being loved and a claim that he had been this way since a child but had always to suppress it. The letter Steele sent to Ferrell is read out, more or less in full I think, and it comes across as manipulative navel-gazing BS.
On the road trip they catch up with various people in Steele’s life, notably with his two shocked-looking teenage daughters, who are stoic in their support for the man they still call Pop, though have to adhere to she/her pronouns for him. There is zero reflection from Steele (or Ferrell) on how his ‘second puberty’ had affected their actual transition from child to young adult, but who expected any different? Also revealing is a visit to Steele’s sister, who also gave unconditional support but still looked grieved. Interestingly, Steele talks of the frilly bell bottoms his sister had given him from her wardrobe in their teens, but because Ferrell is not an interested interrogator we learn nothing further about any childhood crossdressing with mum’s or sister’s clothes, just this hint that it may have happened. Steele chose the name Harper also because his mother went to school with Harper Lee, again no further probing from Ferrell about this, despite it being a possible signpost.
From Steele, we hear that a therapist seven years earlier hadn’t affirmed his gender which sent him into a spiral, close to suicide, forcing him to run away to house he bought in a ‘downtrodden community’, where he secretly wore women’s clothes (I actually wondered about sex parties, but perhaps I’m jaded). Steele talks often about his desire to have been a girl but nothing about what he thinks makes him a woman. Sexist stereotypes/gender roles aren’t even mentioned. We learn that Steele ‘loves his boobs’ and wants to start dating again but there is no clarification of which way his sexuality has now turned (he used to be married to a woman, who divorced him upon his ‘coming out’ it seems). It’s up to a tourist they bump into to ask the most incisive question, she is an ex-therapist and wanted to know what age he ‘knew’. Steele, as ever, sticks to his vague story of always knowing and being trapped. She expresses mortification that she had had a crossdressing man as a client many years earlier, who was wearing his wife’s clothes, and hadn’t been supportive at the time. Steele agrees that being rejected by a therapist is very harmful.
Wherever they go, very few people can tell that Steele is a ‘trans woman’ and have to be repeatedly told by a shouty Ferrell that his friend is actually a lady, though the word ‘she’ never quite rolls off his tongue. Ferrell also has to repeatedly tell people he is Will Ferrell, famous Hollywood actor, but that doesn’t stop him dressing up in disguise several times.
Steele constantly harps on about how unsafe he feels now ‘as a woman’ but this is undermined by two facts: One, he keeps having to tell people he has ‘transitioned’, and, two, no one cares, even in the backwater towns they visit. People do sneer though, as you do when you see a 62 year old man with obvious breast implants. In the documentary this is illustrated by a montage of ‘transphobic’ tweets, which are mildly unpleasant. There is no reflection at any time on serious issues, like that of female sports, single sex spaces, or the transition of children. ‘Bottom surgery’ is mentioned once, with Steele saying he might have it.
As for the friendship between the two, they are clearly close, know each other well but the relationship never gets elevated above just two guys talking around each other, even if there are occasional tears and remonstrations of loyalty. Ferrell shows this by preparing to be the ‘big man’ to Steele’s ‘little woman’, e.g. forking out for the meals they have in restaurants along the way. In order words, indulging sexist stereotypes.
When right at the end of the road trip Ferrell turns to Steele, gifting him a pair of diamond earrings, telling him: ‘It’s okay to feel pretty and do nice pretty things for yourself,’ one realises Ferrell has understood as much as he is capable of. The audience, however, has essentially learnt nothing about his Big Decision. So while Steele has his ‘searching for peace’ narrative in the bag for trans activism, it’s much more of sedative than a direct hit.
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The Lies They Tell 