There is doing a friend a solid and then there’s doing a friend a SOLID. Will Ferrell went above and beyond in his quest to make life easier for recently transitioned friend, Harper Steele. Having a deep love of random Americana, including truck stops and small-town bars, sixty-something Harper Steele wanted one last road trip to explore and enjoy, but this time as Harper Steele, woman.
Harper Steele was assigned male at birth. She came to SNL the same year Will Ferrell started (1995) and the two became fast friends. Twenty-something years later, Harper, after a very long battle with self-identity, transitioned to female. This documentary is -as much as anything else- Harper’s coming out tour, with special guest Will Ferrell.
First of all, I know I said it above, but Ferrell’s actions here are above and beyond. Will Ferrell agreed to drive cross-country with his friend on little more than a whim. Who’s got 17-days to spare for a cross-country US tour, let alone 17 days of being supportive, supportive, supportive? Let’s take away the fact that Harper is now female, traveling to places where they happily enact anti-trans legislation. Do you see yourself doing this for a friend? Suppose it wasn’t a gender reveal tour, but, I dunno, a menopause tour, or a fighting depression tour, or, heck, even a national parks tour. You gotta be comfortable with your friend in a whole lot of ways, no?
Harper Steele can’t hide her voice. It is still deep and unmistakably masculine. This is what throws off many even after seeing Harper’s new rack. Harper announced her transition to Will in letter form, which would floor me. Harper Steele was head writer at SNL for years; how did Will Ferrell not see this as anything but a joke? I guess if you know a person well enough, tone of voice comes across in everything they do, huh?
The two started outside Albany and drove circuitously towards Los Angeles, stopping in many, many places for silly adventure. A unicycle here, a Dunkin’ Donuts, there. The first big reveal happens at a Pacers-Sixers game in Indianapolis. There, the pair meet Governor Eric Holcomb. The Gov was only too happy to meet Will Ferrell; it is revealed after the meet that Governor Holcomb signed anti-trans legislation earlier that year. This really is one of those, “What do you believe?” films. Governor, are you gonna put your mouth where your money is and slam the trans person before you … oh, guess not? Probably not politically expedient in the moment. Had Harper knelt for the national anthem, however, WATCH OUT!
Which is not to say the trip isn’t the ultimate mixed bag – a small crowd of local Native Americans made the twosome feel accepted in 
small-town Oklahoma, however, such was immediately followed by a cosplay steak-eating contest in Texas that proved a serious dud, with plenty of ugly press and ill-wishes following.
It should be pointed out here that Will Ferrell can’t help not being Will Ferrell. As the focal point of every visit where Harper didn’t insist upon going alone, Will Ferrell is the attention getter. Period. When choosing between, “the person with boobs who looks like a man” and “hey, it’s Will Ferrell,” the latter always wins. It won even when Ferrell was in disguise. All of this is a mixed blessing. Will’s natural humor and somewhat infinite patience made the trip enjoyable at most every stop. However, the trip was about Harper Steele; this trip was entirely intended for Harper Steele to introduce herself to America and, at several points during this 17-day journey, The Harper Coming Out Party was pre-empted by the Will Ferrell show.
I found Will & Harper to be simultaneously the most innocuous and the most challenging documentary ever made. We are rooting for Harper, to be certain, and we don’t know if she’ll find acceptance. What could be more innocuous than a person entering a place of business? Ho hum. No biggie. But what if that business is a bar? In a part of the country where morons paint likenesses of Donald Trump on their garages? If you live in a swing state this election season, you’d believe that a candidate could win sheerly on the strength of hating trans people. And that’s what Harper Steele faces every day of her life.
There continues to live a trans woman named Harper
Whose senses needed to be all the sharper
For her trip toured red
Through hate from a to zed
And I’m sure all new friends think she’s a LARPer
Rated R, 114 Minutes
Director: Josh Greenbaum
Writer: Life
Genre: Quest for the mundane
Type of being most likely to enjoy this film: Trans people
Type of being least likely to enjoy this film: Bigots
