Few films drive home travel’s ability to help us understand one another as poignantly as Will & Harper. When Will Ferrell’s longtime friend and Saturday Night Live collaborator Harper Steele comes out as a trans woman, the two set off on a road trip from New York to Los Angeles to better understand her transition and, in turn, their friendship. “I love this country so much,” Harper says. “I just don’t know if it loves me back right now.” Over 17 days, a three-vehicle crew followed the pair and, with mounts on Harper’s Jeep and car-to-car shooting, captured 240 hours of footage. Here, director Josh Greenbaum reflects on the places that moved him and on navigating the country in a new light.
On Location is a column that lifts the curtain on the destinations behind the season’s most exciting new releases, from film and television to music.
Some of the film’s locations like Iowa City and Mojave hold a special meaning for Harper. How did you go about putting those other pins on the map?
At the start of the project, I said to Harper, “This is your and Will’s trip. Map it out, I just need to make sure production can pull it off.” We knew Will would meet Harper upstate before heading west. New York City is special for them, so they started where they first met: Saturday Night Live. Will then wanted to go to DC, where I lost him in the International Spy Museum. He’s calling “Come find me!” and he’s hiding in an air duct. I knew Will and Harper wanted to go to an NBA game because they used to do that together. Iowa City, which you mention, is special because it’s where Harper is from. I remember hitting a patch of snow and saying “Let’s go south,” because it was getting cold up north, so we headed towards Texas. We always wanted to do that southern route and stop along the way. I can’t remember if Vegas was on the original itinerary—neither of them are big Vegas people—but I let Will and Harper steer the road map.
These are roads that Harper has at once traveled down before yet never travelled down as this new version of herself. What do you think that says about coming back to places?
I think we’ve all returned to places years later, which bring out different emotions. I vividly remember the first time I came back to my hometown after being away at university: walking into my house and it feeling different, smelling different. There’s a nostalgia and a distancing that’s sad, yet joyful. For Harper that was much of the experience, because she was rediscovering these places. Returning where she wasn’t sure she could be accepted and then being accepted was powerful. So revisiting places from your past in a new light is a big part of the film.
Grand Canyon and Vegas aside, the trip spotlights some lesser-known places. Harper’s friends poke fun at her for gravitating towards somewhat questionable spots. We see a confederate flag flying in a bar where she surprisingly has some touching encounters—which I think shows a real, nuanced America. Was there a place you felt unexpectedly moved by?
Many. But one that I never thought would elicit the response it did was that dirt race track in a small town called Meeker, Oklahoma. This dad and his son were like, “Come out. If this is what you like, come out.” It was really sweet and—this isn’t in the film—the man came up afterwards and hugged Harper. Then she had this beautiful but heart-wrenching revelation where she says she’s not afraid of other people hating her; she’s afraid of hating herself. That was—as I’m saying it I’m emotional—hard. It was just hard, because I’m also friends with her, so that’s another layer. I knew both of them prior. But to answer your question, I was surprised this was happening at a remote dirt track. I didn’t anticipate an emotional breakthrough at a stock car race.
I found one of the most emotional scenes to be when Harper brings Will to the house she bought for 10 thousand dollars in Mojave, to live in seclusion. But she realizes she doesn’t want to be afraid of people anymore. This says a lot about the hopes and dreams we project onto faraway places, and how coming back might have liberated Harper, just not in the way she’d anticipated. Was being there a pivotal moment for you?
Absolutely. Will knew of that house—Harper had sort of said it off the cuff: “Yeah, I bought a place in the desert.” But he didn’t know what it was or what it represented. When we pulled into the driveway, in this down-and-out town where most people probably go to hide from something, I was already having a hard time not crying from behind the camera. When she revealed that she felt she deserved to live there because she felt like a monster was gut-wrenching. To your earlier question, coming back to this place in a new light, she was able to say “I don’t want this.” She’s since given the house away. She’s living amongst people, friends and loved ones as her true self, so it’s very nice that she shed that thinking.
In contrast to heavier moments, I’m assuming you also laughed a lot. Will and Harper are hilarious: Will screaming at the dogs from the hot air balloon in New Mexico and Harper stating “instead of an asshole, I’ll be a bitch.” Is there a funny story you can share from the trip?
Comedy was critical to the film because they are comedians and I wanted to honor that. We have 240 hours of footage, so there was lots to cut, but in the States we have these billboards of injury attorneys. Will and Harper prank called every one of them. [Bursts out laughing] They’d have conversations about potential lawsuits. Harper also brought a CB radio and the two of them would talk to truckers.
This is why we need to bring back Deleted Scenes.
Yeah! There was a lot of comedy that I unfortunately had to cut.
Beer and Pringles aside, what are your travel essentials?
I never eat it normally, but I need beef jerky on a road trip. And gorp: peanuts, raisins, M&Ms. Trail mix.
After that scene at the steakhouse in Amarillo, Texas, we see a form of violence that’s quite unique to the 21st century: online vitriol. I imagine that even before reading the tweets, the hostility was felt in the room. What was it like capturing that?
It was hard. We had let our guard down because we’d primarily been met with acceptance. Sometimes, love. When we went in, we thought “Oh, Will’s going to try to eat a 72-ounce steak in under an hour, this will be a funny adventure.” I didn’t realize they would be put up on a stage. Will surprised Harper with this Sherlock Holmes costume which added to the problem. But showing up in costumes to surprise each other is something they’ve been doing for decades. I was trying to work that into the film and never found an organic way to say it. But it gutted us. I think if you talk to any trans person, when you’re in a space that feels potentially unsafe, it’s like a threat assessment where you start to feel the room is off, which Harper and then all of us felt quickly. We left dinner early, which was when we became aware of the online, or as you said, subterranean hatred that people for whatever reason feel empowered and safe to do.
“Safe” from behind the screen.
Exactly. But it was important to include it. Because that is part of the trans experience. The worst thing I could have done is paint this it’s-all-sunshine-and-rainbows picture, because it’s not. That said, and I think Harper will agree with this, in general we were met mostly with acceptance, and that notion that it’s hard to hate up close was proven true over and over.
I love that line.
I think when we enter a space and look one another in the eye, as Harper once said to me, our resting place is kindness. And I believe that to be true as well.
Harper says Will was always friends with her because she has always been Harper. But he was also friends with a persona that she doesn’t need anymore. What do you think a road trip says about abandoning personas?
This is true for the American mindset and culture—probably others—where there’s that Jack Kerouac journey, hitting the road to rediscover yourself. We can all get wrapped up in our day-to-day and think “this is who I am,” and it takes breaking patterns in our daily lives to reassess: “Is this who I really am? Can I change? Is there a more authentic version of myself that I’m willing to risk, and share?” I think road trips are one of the better avenues to explore that. There’s also a feeling of adventure, that on any given day, you can take any path. And that fosters this sense of discovery.
When we first see Harper in the film, she puts a record on. She and Will then ask Kristen Wiig to write a theme song for their journey. Is there a personal relevance to the music that was chosen for the film? The soundtrack is amazing.
It’s funny, I usually use a music supervisor to recommend songs, but this time I made a playlist. Music is the fastest way to figure out a film’s tone. Harper’s a music aficionado and has seven or eight thousand records. She sent me the film’s last song ‘Go With Me’ by Gene & Debbe, a band I’d never heard of, among about 40 others and I was like “this one.” She said, “That’s my favorite.” She’d been waiting to put it in a film for a long time. The music you choose is always temporary because you have to clear it. In previous projects I’ve had to change out half the songs because we couldn’t afford them or the artist said no. This is the first project where we got every one. There’s a Bon Iver song, “Holocene,” and everybody was like “Oh, he never lets anyone use it.” But I wrote him a letter and sent him the film, and he said:“Please use it.” Then Kristen wrote that beautiful song.
Will’s fixation on Dunkin’ Donuts and passenger seat tantrum when Harper refuses to stop is too funny. What’s your personal take on Dunkin’?
I’m from the northeast, so it’s probably my go-to for doughnuts. We did just go to Toronto and Will was presented with Tony Hortons doughnut hole—
Tim Hortons!
[Laughs] Tim’s! Will said they were better than Dunkin’ Donuts. I’ll have to taste-test.
Will & Harper is in cinemas now and on Netflix September 27. A version of this story originally appeared on Condé Nast Traveller UK.
