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The Complicated Joy of ‘Will & Harper’

Why did I wait so long to see it?

Tucker Lieberman
3 min readDec 16, 2024
Harper in a checkered blouse rides in the passenger seat. Will in a cowboy shirt is driving. They both laugh. The mountains are behind them in the desert.
Official movie poster

I’ve been hearing about “Will & Harper” for a couple months now, and am glad I finally made the time to watch it.

What happens in this documentary

It’s about the friendship between Will Ferrell and Harper Steele, who joined Saturday Night Live in 1995 and became close friends. Ferrell was a cast member until 2002, and Steele, who was head writer, stayed until 2008.

As Steele passed 60, she transitioned to live as a woman, something she had been thinking about for years. She chose the name Harper because her mother had gone to school with the author Harper Lee. Her two kids and her sister appear in the documentary and share their feelings about her transition.

Steele always enjoyed road trips, stopping at bars in rural areas and chatting with people she meets. But that was when she presented as a man. Post-transition, she isn’t sure whether it’ll be safe for her.

So, in 2023, Ferrell accompanies her on a road trip, an opportunity for him to support her as she confronts her fears. Over 17 days, they reconnect, share their feelings over beer and under fireworks, and experience what their friendship feels like now.

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Tucker Lieberman
Tucker Lieberman

Written by Tucker Lieberman

Cult classic. Author of the novel "Most Famous Short Film of All Time." Editor for Prism & Pen and Identity Current. tuckerlieberman.com

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