While on the Filmmaker Toolkit podcast, director Josh Greenbaum took IndieWire behind the scenes of the planning, making, and editing of his new hit documentary “Will & Harper.” The documentary, which premiered at Sundance and hit Netflix last week, is a road trip film, as comedian Will Ferrell takes a cross-country journey with long-time friend and collaborator Harper Steele after she came out as a transwoman. The journey serves as a way for the two friends to explore how the will affect their friendship, while Steele sees if the country she loves — prior to her transition, Steele loved taking solo cross-country trips and wonders if she can travel the country with the same sense of freedom — will love her back.
Here are nine things about the making of “Will & Harper” that might surprise you, taken from Greenbaum’s Toolkit appearance.
Harper Was Initially Against a Documentary
As the documentary’s opening shows, Steele’s coming out to Ferrell quickly led to the decision to take a road trip, but the part that was left out is that Harper initially didn’t want to film their journey as part of a documentary.
“Harper, I think fairly quickly, not to Will’s surprise, said ‘No, Thank you,’” said Greenbaum while on the podcast. “She has sort of lived her life hiding from cameras.”
This was the case prior to transitioning, as Greenbaum discovered when he was looking for archival footage and photos of his subjects.
“When I was looking for archival footage of her at Saturday Night Live, where she worked for 13 years, and was the head writer, there’s only two photos and [Harper is] in the corner of the frame,” said Greenbaum.
Harper Did Punch-Up On ‘Barb and the Star’
Greenbaum has known Ferrell and Steele for a few years, and considered them friends before making “Will & Harper.” Ferrell produced the director’s “Barb and the Star Go to the Vista Del Mar,” and starred in his film “Strays.”
“I actually knew Harper as well prior,” said Greenbaum. “Kristen Wiig introduced me to her. She came in while making ‘Barb and Star’ as a writer doing some punch up, roundtable kind of stuff.”
Greenbaum said knowing the two subjects turned out to be helpful in making the film, as was the fact that he has a unique career that bridges both comedy and documentaries (“Becoming Bond,” “Too Funny to Fail: The Life & Death of the Dana Carvey Show”). That combination made him the logical director for “Will & Harper,” but that’s not how he got the job.
“The real backstory, that’s also pretty fun,” said Greenbaum. “After Will had the idea for the film, he was telling his business partner, Jessica Elbaum, who is the head of Gloria Sanchez, their company, who did produce ‘Barb and Star,’ and she said, ‘Oh, this sounds amazing, but we don’t make docs.’”
Elbaum’s husband, Rafael Marmor, had worked in nonfiction for decades and was who the Gloria Sanchez head turned to for guidance.
“Rafi happens to be one of my oldest friends of 20 years from college; he’s also produced all seven of my doc projects,“ said Greenbaum, who on three different fronts seems to have been destined to direct “Will & Harper.”
The Opening Sequence Was Originally Its Sales Reel
The opening minutes of “Will & Harper” is an incredibly condensed and breezy retelling of the two friends’ professional history together, Steele coming out to Ferrell, and the decision to take the road trip. It’s a perfect distillation of the film’s premise, which is why it also made for an effective sales reel.
“I shot all of that, which you see as the opening of the film, to essentially create a pitch reel, a sizzle reel as we call it, to go get funding,” said Greenbaum. “This is not uncommon in docs that I’ve done in the past, whereby I create some sort sizzle reel trailer, something that conveys what the film may be about, take that out to independent financiers to find financing. And then I find time and time again, I use a version of that thing as the opening of the film itself.”
Astute and repeated viewers of the film will notice how the film’s opening is shot in a completely different style from what follows, with Steele and Ferrell talking to the camera, and a slate that reads “untitled road trip movie.”
The Director’s Biggest Fear
Nonfiction filmmakers can structure narrative in the editing room, but there wasn’t a ton of room to fudge the timeline in “Will & Harper. ” The film is a linear road trip across the country, and each region has a unique landscape and distinct backdrop.
“This was one of my biggest fears when I launched into the project,” said Greenbaum. “In docs I tend to get out of the way and just let whatever happens happen, and then shape it in the edit. And I think it hit me early on that like, ‘Oh God, what if they have one of the most profound conversations on day one, sort of climax of the film, the emotional climax happens on day two. Traditionally you might in a doc be able to move those things around in the edit, but here you can see when they’re in upstate New York (the start of the journey) versus Arizona and California.”
Greenbaum said one thing he had going for him was it’s human nature to not launch into the deepest, most difficult question right away. But he took some precautions.
“I knew they had questions for one another. Like Will had a lot of questions he wanted to ask Harper, and she wanted to ask him. And I said, ‘Why don’t you both send me all of the questions and conversations you want to have? Don’t share them with each other,’” said Greenbaum. “And that way I have a little bit of what I was calling our ‘Question Conversation Bible.’”
The director said by and large the conversations happened naturally, and didn’t come too early or too late in the road-trip/narrative arc, but that a few times throughout the trip he’d remind Steele or Ferrell of questions at what felt like the right time in the 17 day trip.
Car Scenes: Cameras Were Always Rolling
While Greenbaum might have tried to space out and map out the big questions Harper and Will asked each other as they drove, that does not mean the cameras went on and off.
“When we were driving, we were rolling pretty much the entire time,” said Greenbaum, who went into the edit with 240 hours of footage from a 17 day trip. “They were worried early on whether or not they could talk for 16, 17 days straight. And they did because I also didn’t let them listen to music in the car.”
That’s right. This was a road trip with no music, which seems hard to imagine but makes perfect sense from a filmmaking standpoint—Greenbaum couldn’t let unlicensed music on Steele and Ferrell’s audio tracks. Never knowing what moments would end up in the film, he didn’t want footage rendered unusable because he couldn’t license or afford to license the music underneath their dialogue.
That Oklahoma Bar
If you’ve seen “Will & Harper,” no doubt Steele’s first visit to a roadside bar in Oklahoma is one you remember. It’s the type of honky tonk place she visited all the time as a man but wonders if she’ll be safe in as a trans woman. And according to Greenbaum, the scene was just as nervewracking for the crew as it was to watch.
“I walked in to just pre-scout it with my DP five minutes before we’re about to go in,” said Greenbaum. “And I of course see the Confederate flag, I see the “fuck Biden,” the Trump [banner], and everyone’s smoking, it’s lawless. And I came back out to say to Harper, ‘I want you to know all of this, what it looks like in there, and we can go find a different bar.”
Steele was insistent and entered the bar. The cameras that followed here were not hidden, but they were long-lens and the camera operators gravitated to the corners of the room. That night, there was a pool tournament drawing the patrons’ attention, some of whom may have noticed the cameras and possibly thought they were filming the tournament.
“Will’s nervous, I’m nervous,” said Greenbaum. “We did have a security person for this. Luckily, they never had to do anything. I always want to protect my subjects, but these are close friends of mine.”
The Costumes & the Painful Big Texan Scene
It didn’t take long for Ferrell to realize dressing up as Sherlock Holmes and making a show of trying to eat the 72-ounce steak at the Big Texan restaurant was a mistake, garnering unwelcome attention. You can see in the film how badly he feels afterwards — breaking into tears, realizing he’s hurt Steele, as well as having created an unsafe space for his friend. Greenbaum said the moment was a collective mistake born out of a string of positive experiences they had had, like the bar in Oklahoma.
“I think we got lulled into a sense of security and confidence,” said Greenbaum. “We had been sort of met with nothing but love and or acceptance and warmth overall, and it goes back to that notion that it’s hard to hate up close.”
To Ferrell’s credit, Greenbaum notes, the famous comedian never flinched at including this scene in the movie, which wasn’t something the director ever really considered. He admits he was nervous to show the film to Steele and Ferrell, but was pleasantly surprised the response was tears, rather than notes.
“Will was willing to fuck up, and that’s so helpful. I think what’s happening in this space and other spaces is people are so afraid to fuck up, which I get. It’s like, ‘I want to say the perfect thing, the right thing. I don’t want to say the wrong thing. I want to be an ally. I want to be supportive, but I don’t want to say the wrong thing,’” said Greenbaum. “And what you see in our film, and in Harper and Will’s relationship, is Harper affords Will a lot of grace. But Will’s also willing to show himself, warts and all, make the mistakes, fuck up, and only through that does growth and dialogue happen.”
And not to make an excuse for Ferrell’s blunder, but there was a backstory to him dressing up in a costume.
“I didn’t get to work this into the film, but they both love costumes,” said Greenbaum. “And in fact, I found out that over their 30 year friendship, one of their favorite things to do would be to go to a party, and not a costume party, and both of them show up in costume, not telling each other what they were wearing.”
Harper’s Desert Hideaway
It’s the most heart-wrenching scene in the film, when the road trip enters Trona, California, and Steele brings Ferrell to the home she bought in the middle of nowhere, just outside the Mojave Desert.
“Will, he really had no idea, because she bought it six, seven years ago and had told Will and friends, ‘I bought this place for 10,000 bucks up in the desert, I’m going to turn it into something cool,” said Greenbaum. ”And she does that all the time, she’s like very handy. And so I think to Will and all of Harper’s friends, it was a project.”
When mapping out the road trip and documentary, Steele didn’t reveal much about the place to Greenbaum, simply mentioning “it could be an interesting place to stop” and subtly indicating it was a “darker place for her.” But nothing prepared the director and crew for what would transpire.
“When we pulled up, I remember just already getting emotional and gutted by not only just pulling into that town, which is this very down and out town — where I think you get the sense probably a lot of people go to hide away from something in their lives — and then pulling up to her house and seeing the state of disrepair it was [in],” said Greenbaum. “It ultimately is very clearly, she said, ‘I wanted to move here and live my life out here in hiding where I could live my life as a woman, dress in women’s clothes, but not be around anyone. It’s devastating to think that at some point, that’s where she thought she deserved. It was a shock certainly to all of us then as we worked our way through inside the house, which you can see was vandalized and it was really a hard, emotional, profound moment, but again, a beautiful one ultimately of growth as you see in the film.”
In the film, Steele says that she doesn’t want this anymore, and Greenbaum is happy to report that this is very true.
“I can tell you since then, she’s given the house away,” said Greenbaum. “She lives not far from me in Burbank, California. We go and get beers on the regular at our local little dive bar.”
Bon Iver, Pringles, and Dunkin’ Donuts
Greenbaum said there are two common misconnections about “Will & Harper: ” One, that they had a huge music budget due to the number of songs by famous bands, and two, that they received product placement dollars from Pringles and Dunkin’ Donuts. There was no product placement; that’s all Steele and Ferrell—both their love of junk food and commitment to a bit.
Greenbaum said making a Gloria Sanchez documentary featuring Will Ferrell did not mean some outsized music budget, and he was warned the music he was temping to while editing was a mistake. In particular, “Holocene” by Bon Iver, which plays during the cathartic fireworks scene after Ferrell and Steele visit the Trona hideaway.
“I was told by every friend of mine, every music supervisor, just get the song out now before you fall more in love with it, because you’ll never get it,” said Greenbaum.
Greenbaum credits music supervisor Joey Singer for getting the rights to every track, including “Holocene,” but adds that the film’s subject matter was an easier than imagine selling point to artists like Bon Iver, who are hesistant to license out their music.
“I sent Justin Vernon, Bon Iver, a letter,” said Greenbaum. “I sent the film in [as well] and he said back, ‘Please use it. Go for it.’”
Will & Harper is streaming on Netflix.
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