Madonna

No artist worked the music video harder than Madonna, or treated it less like an afterthought. Twice she picked a director the same way — by chasing a clip that had impressed her. She went after Steve Barron in 1983 because of what he had done with Billie Jean, and fifteen years later called Chris Cunningham after seeing his Come to Daddy film for Aphex Twin. In between came Mary Lambert, who directed five of the early ones, and then David Fincher, Jean-Baptiste Mondino, Herb Ritts, Mark Romanek and Jonas Åkerlund.

The roster matters because she kept moving. Lambert gave her the white lace of Like a Virgin and the Catholic imagery running through La Isla Bonita and Like a Prayer. Fincher answered with stylised black and white — the machine-room futurism of Express Yourself, then the studio portraiture of Vogue. Cunningham shot her in the Mojave as a shape-shifting figure who dissolves into ravens and dogs. Where most artists settle into one visual identity, she treated each album as a reason to hire a different eye.

Two clips carried real consequences. Like a Prayer (1989) set burning crosses and a Black saint against a gospel choir, and Pepsi cancelled a multimillion-dollar sponsorship within days. Justify My Love (1990), directed by Mondino, was refused outright by MTV and sold as a video single instead — proof that a banned clip could still find its audience.