Directed by Your Favorite Singer

June 11, 2019

Lots of musicians have given acting a try, like Cher and Eminem. A few have taken an even larger jump—from singing and writing songs…to directing movies. It hasn’t always gone very well.


After more than two decades of lacing her songs and videos with provocative themes and adults-only imagery, respectively, Madonna took the reins on her own suggestive, full-length project. In 2008, the Material Girl directed Filth and Wisdom,a musical dramedy about a Ukrainian immigrant living in London who makes a living as a prostitute (while posing as a woman). His roommate is a ballet dancer who pays the bills by stripping. Critics didn’t care for Filth and Wisdom, particularly Ben Mankiewicz of At the Movies who called it “a terrible, terrible worthless movie.”


Perhaps the greatest American crooner of the 20th century and the biggest pre-rock n’ roll teen idol, Frank Sinatra could also act, earning Academy Award nominations for The Man with the Golden Arm and From Here to Eternity (for which he won). He also directed exactly one movie: the World War II-set None But the Brave (1965) that earned middling critical reviews, in part because it took the then bold tactic of presenting some of the action from the point of view of Japanese soldiers.


Dylan won the Nobel Prize for his lyric writing and effect on the world’s culture…not for his 1978 directorial debut Renaldo and Clara. It’s a four-hour mixture of concert footage of Dylan performing, Dylan backstage and touring from town to town, and an impossible to follow, completely abstract dramatic “story.” At various points, Dylan appears in “whiteface,” folk singer Joan Baez plays a mysterious “Woman in White,” and there’s another inscrutable character named “The Masked Tortilla.”


The quirky, low-budget 1982 dark comedy Human Highway bears a “Directed by Bernard Shakey” credit, but don’t be fooled—it’s a pseudonym for rock legend Neil Young. Marketed as a “surreal nuclear comedy,” it’s about the comings and goings at a gas station and diner situated next to a nuclear power plant on the last day of existence before the Earth is destroyed. Some of the business’s patrons include Dennis Hopper, the New Wave band Devo, and Neil Young himself.