Will & Harper – a charming but impersonal road… | Little White Lies

Will & Harp­er – a charm­ing but imper­son­al road trip movie

11 Sep 2024 / Released: 13 Sep 2024

Words by Juan Barquin

Directed by Josh Greenbaum

Starring Harper Steele and Will Ferrell

Two people taking a selfie in front of a "Welcome to Texas" sign.
Two people taking a selfie in front of a "Welcome to Texas" sign.
4

Anticipation.

Two comedians on a road trip? Sign me up.

3

Enjoyment.

As fun and boring as any extended car ride.

3

In Retrospect.

Its casual charm lingers beyond dull educational beats.

Will Fer­rell and his best friend Harp­er Steele embark on a cross-coun­try road trip, reflect­ing on Steele’s expe­ri­ences as a recent­ly out trans woman, in Josh Green­baum’s mean­der­ing but sweet documentary.

If coun­try roads were designed to take one home to the place they belong, what of those who find them­selves at odds with the very roads they once found solace in? This is pre­cise­ly what Josh Greenbaum’s Will & Harp­er ques­tions as it fol­lows for­mer SNL writer Harp­er Steele (a recent­ly out trans woman) and her best friend (Will Fer­rell) on a road trip across the USA.

It’s a sim­ple premise for a sim­ple movie – one that spends its run­time serv­ing as some­thing of an extend­ed ther­a­py ses­sion for Steele. Or per­haps it’s more rea­son­able to call it expo­sure ther­a­py, com­plete with Steele open­ing her­self up to friends and strangers alike for mild­ly intru­sive ques­tions, plen­ty of mis­gen­der­ing, and sin­cere­ly heart­break­ing per­son­al rev­e­la­tions of what exist­ing as clos­et­ed did to her.

For Steele, trav­el­ling across the coun­try while pre­sent­ing as male was a source of com­fort, tak­ing great plea­sure in find­ing dive bars and seedy joints to vibe with strangers. It’s heart­break­ing to watch her explain how much anx­i­ety she has over some­thing she used to love sim­ply because of her tran­si­tion, but that is exact­ly why Fer­rell is there. He is both a pil­lar of sup­port and a means of bring­ing out the laugh­ter and joy that exists in Harp­er, and there’s some­thing beau­ti­ful about the way the two bounce back and forth sometimes.

The thing about Will & Harp­er is that so much of it feels pol­ished to the point of unbe­liev­abil­i­ty. Ferrell’s fame obvi­ous­ly offers some lev­el of safe­ty net, as does the pres­ence of an unhid­den cam­era, but it extends beyond that. Where casu­al con­ver­sa­tions between the title char­ac­ters” come across as hon­est and play­ful, as do those with peo­ple from Harper’s own life (includ­ing her chil­dren), many of the set-ups with strangers across Amer­i­ca come across as not quite staged, but cer­tain­ly scout­ed for safe­ty and san­i­tized to the point of ques­tion­ing their verac­i­ty. There’s no urgency, no dan­ger, which is cer­tain­ly bet­ter for the trans woman at its core, but it makes these scenes fall flat and there’s not much Green­baum can do to enliv­en them.

This kind of neu­tral­i­ty is some­thing that’s per­fect for a cis audi­ence inex­pe­ri­enced with any­thing trans, but it makes one long for more of the highs and lows that the film show­cas­es. An extend­ed bit with anoth­er trans woman that Harp­er met in the past, where the two dis­cuss their expe­ri­ences, is gen­uine­ly love­ly and reveal­ing, as is one of Harper’s low­est points where she reveals the lengths she took to ini­tial­ly tran­si­tion and how much she felt like a mon­ster. All the cameos from for­mer SNL play­ers and writ­ers (save for Kris­ten Wiig, who is asked by the duo to write a sil­ly lit­tle song for their road trip) weigh the film down, but pre­sum­ably serve as anoth­er lay­er of relata­bil­i­ty, or nor­mal­cy”, for an audi­ence unfa­mil­iar” with trans people.

Its lack of any the­sis oth­er than bare-bones edu­ca­tion makes Will & Harp­er a hard film to label. It’s a doc­u­men­tary that feels a lit­tle too delib­er­ate­ly man­i­cured for its own good, it’s not enough of a por­trait of these small Amer­i­can towns to be con­sid­ered a trav­el­ogue, it’s not espe­cial­ly edu­ca­tion­al in the way it pur­ports, and it isn’t par­tic­u­lar­ly fun­ny enough to be much of a com­e­dy. As such, it’s just float­ing in a no-man’s land, a charm­ing but imper­son­al film about a deeply per­son­al journey.

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