Thursday, March 5, 2026

Will & Harper:
A Documentary About Trans Identity and Friendship

Michelle over at Between Genders recently published a review of the documentary Will & Harper, which follows actor Will Ferrell and his close friend Harper Steele as they travel across the United States together. Along the way, the pair reflect on their friendship while discussing identity, acceptance, and change after Steele comes out as a trans woman.

After reading Michelle’s review (read HERE), I decided to give the documentary a watch myself. I was particularly intrigued by the premise, as I’ve often wondered what it must feel like to come out later in life and begin living openly as a trans woman.

Harper Steele and Will Ferrell

At the beginning of the documentary it is revealed that in 2021 Will Ferrell received an email from his longtime friend and former Saturday Night Live colleague Harper Steele, in which she shared that she was transgender. Two years later, Steele and Ferrell meet with Steele’s daughters at a restaurant before setting off on their road trip. The pair begin in New York City, first visiting Studio 8H and reuniting with several Saturday Night Live cast members.

Ferrell and Steele then travel to Washington, DC, where they discuss Steele’s identity and their friendship in a car park while briefly meeting a fan. From there they head to Beech Grove, Indiana, where they attend a basketball game and encounter Governor Eric Holcomb. Shortly afterwards, they learn that Holcomb has signed a bill banning gender-affirming care for minors in Indiana, and they hear further reports about anti-trans legislation across the country.

Their journey continues to Peoria, Illinois, where they meet another trans woman named Dana, who also transitioned later in life. Dana speaks about how her childhood was shaped by the painful mismatch between her gender identity and how others perceived her.

While travelling to Iowa City, Ferrell and Steele contact actress and comedian Kristen Wiig and ask if she would write a song inspired by their road trip. In Iowa City they meet Steele’s sister, Eleanor, and Steele recalls a childhood story about receiving a pair of frilly bell-bottoms from her. Although she loved them, she stopped wearing them after being subjected to homophobic slurs. Steele also reflects on her childhood while looking through baby photos and visiting her childhood home.

The pair then travel to Meeker, Oklahoma, where Steele enters a dive bar alone before asking Ferrell to join her. Later they stop at a steakhouse in Amarillo, Texas, where social media comments about Steele are revealed to be filled with prejudice. Ferrell attempts to lighten the atmosphere by dressing up as Sherlock Holmes, but the joke backfires when it unintentionally draws attention to Steele and her trans identity. Looking back on the encounter, Ferrell later reflects that the atmosphere was extremely transphobic, though he admits he struggled to fully grasp Steele’s fears at the time. During the journey that follows, Steele opens up about having previously experienced suicidal thoughts, which had made her deliberately avoid buying a gun.

Next they travel to Albuquerque, New Mexico, where they take a hot-air balloon ride with actor, comedian, writer, and producer Will Forte. Afterwards they visit the Grand Canyon, where a woman takes their photograph and shares that she is a retired therapist who once had a patient with gender dysphoria. She admits that she was regretfully close-minded at the time.

From there the pair head to Las Vegas, where they dine at SW Steakhouse. Beforehand, Steele buys a dress and has her makeup done, while Ferrell purchases a wig and moustache in an attempt to disguise himself. During dinner Steele acknowledges that Ferrell’s presence may have shielded her from some open transphobia, but she also credits their journey together with helping her grow in confidence.

Later they visit Trona in San Bernardino County, California, where Steele shows Ferrell a house she had purchased several years earlier. It had been intended as a place of escape, somewhere she could live privately as a woman before publicly transitioning. The house is now vandalised and in disrepair, although the film does not make clear how this happened. The moment becomes one of the documentary’s most emotional scenes, as Steele breaks down and Ferrell comforts her.

On the final day of their road trip, Steele finally gives in to Ferrell’s long-running request for Dunkin’ Donuts after he had been asking for them throughout the journey. Their final destination is Los Angeles, where they first visit a nail salon with actress and comedian Molly Shannon. There, they reflect on what they have learned about one another during the trip. Afterwards they head to the beach, where Steele and Ferrell reminisce about their friendship, the experiences they’ve shared, and what the future might hold. Ferrell gifts Steele a pair of diamond earrings, and Steele suggests that they should one day take another road trip back to New York City, an idea Ferrell happily agrees to.

 
Harper Steele

As the film concludes, it is revealed that Wiig has finished the song inspired by their journey, titled “Harper and Will Go West.” The song plays over the closing credits alongside miscellaneous footage from their trip.

Overall, I found Will & Harper to be a very watchable documentary, balancing both sad and genuinely funny moments throughout the journey. The moment that resonated with me most was when Harper spoke openly about her past suicidal thoughts. Hearing her describe those feelings immediately struck a chord with me, as it’s a place I’ve unfortunately been myself.

There are lighter moments too. One that stood out was when they attempted the famous 72-ounce steak challenge at the Big Texan Steak Ranch in Amarillo, Texas. I have a pretty healthy appetite, but even I’d struggle to finish that enormous steak and all the sides within an hour!
 
If you haven't see documentary already, definitely check it out.
 
Thanks for reading,
 
Lotte x 

6 comments:

  1. It's been a while since we watched the film, but I remember enjoying it. From what I recall, Will did his best to understand what Harper is going through, and he doesn't always get it right. I thought that Harper's gentle forgiveness and funny retorts really highlighted their friendship.

    I did feel for Harper given the time she grew up in, and that she felt she had to hide who she was fit so long. I seem to remember her grown-up children were very cool about things.

    As to the steak, is 72oz about two kilogrammes? I'm not sure i could eat 2kg of anything in one go! No judgement, just surprise.

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    1. Yeah I thought that too Lynn about Will doing his best to understand what Harper is going through and not always getting it right.

      Yes, it must have been very hard growing up in that time and having to hide away.

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  2. I'm glad you saw the doc and am promoting it. I watched it a year or two ago and was pleasantly surprised. I dislike Will's comedic films but was impressed with his humanity here: he showed how real friends should act in supporting others.

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    1. Thanks Ally, yeah thought it was worth promoting for all the right reasons.

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  3. I enjoyed the film because it shows how true friends will be there for each other, and it also showed how someone can change through gender transition and yet still be the same person they always were. And it shows that with a little understanding and a lot of friendship on both sides, the initial awkwardness of the situation can soon evaporate as long as everyone is patient and willing to understand each other. I think it's a powerful film given what's happening at the moment and I really enjoyed it.

    Dee xxx

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    1. Thank you for your thoughtful comment Dee. I completely agree with your points and appreciate you sharing your perspective x

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