Will Ferrell and Harper Steele were friends from their Saturday Night Live days. Ferrell became one of the breakout stars of the popular sketch comedy show where Steele was the head writer from 2004 to 2008. The two continued to be friends and collaborators, going to games and dive bars and co-writing the glorious Eurovision Song Contest: The Story of Fire Saga .
Steele came out as a transwoman in 2021. “The biggest question when people come out of the closet is, ‘Will I still be loved’,” she says in their documentary Will & Harper . Ferrell and Steele undertake a road trip from New York to Los Angeles, as a way of coming out to America with Ferrell’s celebrity as a cushion against the slings and arrows of outrage.
The road trip is also a way of strengthening the bond between them, to see what, if anything has changed. The differences are there from the packing stage itself, where earlier as a man, she would pack a couple of tee-shirts, a pair of jeans and underwear, now Steele has a tough time just choosing the shoes to pack! After packing up the road trip essentials, which include, according to Steele, “chairs, a cooler and a natty beer,” the two set off from New York with a stop at SNL studios where they meet their former colleagues and friends including Tina Fey. On the 16-day trip across America, they meet people in bars and gas stations.
At The Grand Canyon, they meet a therapist who poignantly confesses to being unable to help a patient. They also meet Ha.