"Will & Harper" with Josh Greenbaum

Top Docs: Award-Winning Documentary Filmmakers

Road trips — and road trip movies — are as American as apple pie. And now, currently streaming on Netflix, we have director Josh Greenbaum’s poignant and very funny documentary “Will & Harper,” which tags along on a cross country road trip with close friends Will Ferrell and Harper Steele as the two navigate Harper’s recent transition as a woman. Since meeting during their first week on staff together at “Saturday Night Love,” they’ve been tight ever since. But when Harper sends Will an email coming out as a trans woman, she can’t be sure how her famous comedian friend will react. In short order, Will proposes a road trip so that they can ask all those questions that arise after such a big change.

Director Josh Greenbaum joins Ken on the pod to discuss all the joys and bumps on the road that transpired over the course of Will and Harper’s epic 16-day journey to such noted tourist destinations as the Grand Canyon… and a dive bar in Meeker, Oklahoma. Along the way, the two tackle such questions as, “What are the new ground rules for the friendship, if any?” “Can Harper still feel safe and comfortable in the same kind of places she used to visit as a man?” And “How are your boobs??” The laughs and the tears come in equal measure. Buckle up and enjoy the ride.

“Will & Harper” has recently been named to the Oscar Shortlist for Best Documentary Feature, and “Harper and Will Go West,” the theme song for the trip written by Kristin Wiig, has been named to the Oscar Shortlist for Best Original Song.

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