US actor and comedian Will Ferrell hits the road with old friend, transgender woman Harper Steele in new doco

Harper Steele talks about her transition with Will Ferrell on their road trip, as he enters uncharted territory on what he knows about the transgender community.

Harper Steele talks about her transition with Will Ferrell on their road trip, as he enters uncharted territory on what he knows about the transgender community. Photo: Twitter

He might be more familiar in hilarious films like Anchorman or Elf, but US celebrity, actor and comedian Will Ferrell has turned his talents to a more heartwarming project on screen.

Teaming up with transgender best friend and former Saturday Night Live writer Harper Steele, the pair are front and centre in a fly-on-the-wall documentary, Will and Harper, about their 16-day road trip from New York City to the Santa Monica Pier in Los Angeles.

The reason was simple.

After Ferrell, who had first worked with Steele back in the 1990s on SNL, received a long coming-out email from Steele describing her decision to transition at 61, he suggested they travel the country together.

“For me, it was a chance to transition myself, in a way – to learn, to get to know my friend even more than I knew her before, to get to ask these questions that I think a lot of cis people [gender from birth] still have, for me to struggle on camera with asking these questions,” Ferrell told a Deadline Studio at Sundance panel chat after the premiere on January 22.

“And then there are a couple of emotional moments where I’m struggling with making sure I stand up for my friend in moments that felt tense for us and feeling like I fail at times.

“But I think we were obviously both willing to go there. That’s kind of crazy about a documentary – you do eventually forget there are cameras there and we let our guard down and we’re able to have these super honest and kind of frank discussions.”

For Steele, it was a chance to visit the bars and dives she frequented as a man, whether she would be insulted or attacked, and have new conversations with Ferrell.

“What the doc did for me was give me a little more confidence as a trans woman. I will say you probably don’t want to be overly confident. I’m still a little leery of what I would do in my 20s and 30s when I was performing male, but I think I am a lot more confident,” Steele said.

“I think this documentary helped me immensely in that sense”.

Ferrell in uncharted territory

Ferrell, 56, is no stranger to making films and television series.

His latest role, playing Mattel boss in the Greta Gerwig Barbie movie, comes off a string of movie credits in the 2000s including Talladega Nights, Blades of Glory, Step Brothers, The Other Guys and Get Hard in 2015.

He’s ventured into a few dramatic roles, had voice-over roles in Megamind and The Lego Movie film franchise (2014 to 2019) and was producer on award-winning drama series, Succession, for four years.

He says Will and Harper was a chance to try and understand and support his friend (Steele grew up in Iowa] and take the subject matter to a mainstream audience where the LBGTQI community continues to face discrimination.

At points across the US, Ferrell broke down in tears.

Harper Steele and Will Ferrell at the Variety Sundance Studio on January 21. Photo: Getty

After the documentary’s screening at the Sundance Film Festival earlier this week, some critics applauded the film for its positivity, Ferrell’s comedic control, and “opting instead to emphasise how welcoming complete strangers are to Steele wherever she goes”.

Others, including IndieWire‘s Lauren Wissot, says it was well intentioned, but was played “too straight” with the intention of not offending anyone.

“Ferrell does take the opportunity to pose questions – not the tough stuff that sceptics and haters might lob, but personal inquiries, like how Steele chose her new name, whether she’s thinking about bottom surgery and what kind of partner she sees herself with in the future,” writes Variety’s Peter Debruge.

Either way, Debruge goes one step further and says this is the documentary the world needs right now.

“This down-to-earth trip will likely prove even more important for a different audience – namely, those with gender dysphoria issues of their own, who see in Steele a role model.

“Coming out can be incredibly scary, and Steele is eloquent and open about her fears.”

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