Will Ferrell, Harper Steele, and Director Josh Greenbaum Discuss ‘Will & Harper’ Documentary | TIFF 2024

Will & Harper, a documentary about friendship and the transgender experience, follows former Saturday Night Live coworkers Will Ferrell and Harper Steele. The two reunite for a road trip across America as Ferrell helps Steele feel more comfortable in different spaces after transitioning.

After the film’s premiere at the Toronto International Film Festival, stars Ferrell and Steele and director Josh Greenbaum stayed for a Q&A with the audience.

Before the questions could start, the three were met with a standing ovation that lasted several minutes and had Ferrell visibly choked up. “No one has ever liked Will this much,” Steele joked.

Ferrell admitted he didn’t believe the hours of footage they shot would amount to anything, let alone a film the audience could engage with.

“We’re sitting on the beach for the final shot, and I turn to Harper and say, ‘I don’t think there’s a movie there. I mean, that was fun, but good luck,'” Ferrell chuckled.

“Months go by, and when Josh [Greenbaum] finally showed us something, we were both in disbelief. Josh somehow found a way to make it funny, to make it emotional, and to find a narrative through-line there that keeps you engaged. It plays like a movie, and we were like, ‘How did you do that?'”

“Cinema,” Greenbaum responded with a grin.

After years of creating characters for SNL and films, this documentary required the two friends to play themselves, which could sometimes be daunting.

“It’s an unusual experience. Josh warned us that it would be a few days before we got comfortable with what was happening,” Steele explained. “And fortunately, having done a lot of documentaries, he was correct about that.”

“That was the second year of my transition, so I was looking for ways to express myself more, and I thought this documentary might do a great job there.”

“And there were a lot of bills in the US that were being passed, decided on, and introduced into legislation all across the country that were against me, against children, against human rights issues that I cared about. And I was like, well, maybe I can use this universally beloved doofus [Ferrell].”

Thankfully, Steele and Ferrel’s love language managed to prevail.

“We forgot the cameras were there, and what you see is not much different than our relationship of seven years. The best laugh I can get in this world is to make Will laugh. That’s what we do with our lives. It just had this new informative wrinkle that worked well with that conversation — our love language, which is comedy.”

But if you think this kept the two SNL alums from trying to sneak a bit or two into the film, think again.

“Oh, there’s some fantastic character work that is on the cutting room floor,” Ferrell revealed.

“Harper brought a CB radio. It’s not in the film, but he [Ferrell] took on the role of a trucker at one point and started talking to a lot of truckers,” Greenbaum recalled. “They called a lot of lawyers from billboards.”

“I think I called every personal injury lawyer. We were doing prank calls, you know, to amuse ourselves,” Ferrell added.

Steele could confirm Ferrell was very committed to this particular bit. “You’d be in the middle of a conversation. It’s like, ‘-and then I started taking the estrogen,’ and Will would go, ‘Oh, look! It says to call Keith Skyler. Let’s call them.'”

“No, I will defend you!” Ferrell mocked.

Jokes aside, Ferrell admitted it was challenging to rein in the comedian side of his brain, and he had to be careful not to ruin a powerful scene with a joke.

“One of my favorite scenes is at the Grand Canyon where this woman, who’s the retired therapist, comes up,and they have this beautiful exchange where she’s almost making amends for a past patient of hers. Harper gets to counsel her and this is great moment,” Ferrell explains to the crowd.

“And I really had to turn off my comedy brain, because, as Harper says, ‘Oh, I used to have a therapist who gave me that advice.’ I almost went, ‘Are you that therapist?’ And I went, ‘No, just listen and shut up!'”

“It is hard to pass those things up,” Greenbaum interjected. “Ugh yeah, but I’m happy I didn’t because that’s a great moment,” Ferrell responded.

In the film, Ferrell and Steele’s pit stop at a steak house in Texas quickly became a defining moment of the documentary for all the wrong reasons, as a hostile crowd of onlookers formed around the two during their meal.

Steele kept an open mind when speaking about the “judgment” she faced. “I’m very hesitant to generalize about a large crowd of people or a state like Texas or because there are good people in all these places,” she admitted.

“But as a trans person who doesn’t pass, I’m not very invisible. You can feel a crowd. You can feel people looking at you, and you might project some fear. And sometimes that’s not good. However, the crowd was excited that Will was there. I’ll be honest; they were not excited that he showed up as Sherlock Holmes.”

“They wanted Ricky Bobby,” Ferrell added. Steele felt it was a perfect choice: “They got Sherlock Holmes. That’s what they deserved.”

Steele reflected further on what made that experience unsettling for her. “Very quickly, that environment felt threatening — that’s the wrong word because violence was not in the air. It’s a kind of oppressive judgment we don’t need in this world, and that’s what I felt. Through osmosis, Will began to feel the same thing.”

“It threw me because this was going to be one of those fun road trip stops, eat the 72-hour steak in an hour. Keep in mind, read the fine print. You must also eat two fried shrimp, an entire baked potato, and some wilted broccoli. So it’s not just a steak,” Ferrell explained, some lingering anger still present.

“It’s a total it’s a ruse,” Ferrell disclosed. “Regardless, we thought it was just going to be this light, benign place to stop. That’s why I felt like, ‘Ah, I didn’t mean to put you in that situation,’ and that’s why I felt such emotion the next day.”

The Q&A concluded with a moment of reflection on how films like Will & Harper help shed light on the everyday kindness and acceptance that doesn’t make the news.

“See, this is politicians and press. This is not America,” Steele lamented as she addressed the fear-mongering that currently surrounds the transgender discussion.

“I feel like the general movement is in the right direction. I’m very optimistic about the human character of Americans. I think we like to be neighborly, and I’m fairly optimistic. But again, that’s with a caveat that it is not safe for a lot of trans people out there. We’re more likely to get violence against us than almost any demographic. So I’m aware of that, but I try to remain optimistic.”

“The expression that it’s hard to hate up close just kept becoming true over and over,” Greenbaum added about their time filming.

“You know, 70% of people don’t directly know a trans person, and so to Harper’s point, they’re getting it from politicians, the media, etc. That’s why stories like this, and there are many other wonderful trans stories besides our film, are important. You watch this film and know Harper, and what a great person to know, right?”

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Will & Harper is now streaming on Netflix. Check out our review of the documentary right here!

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