5. Sting “Englishman In New York” (1998)
A lovely tribute to Quentin Crisp, about whom the song was written and who features in the video, this is also a criminally lovely black and white snapshot of New York that almost rivals “Manhattan” in the sheer force of its affection for the city.
4. Madonna “Express Yourself” (1989)
The following year may have been Fincher’s Annus Mirabilis as far as videos go, but it was this Madonna spot that really broke him into the upper echelons.
 From the striking dystopian, anti-capitalist imagery, to Madonna in a suit sporting a monocle, to the massive steampunky cogs and gears, to that ridiculously memorable shot of Madge spilling the saucer of milk over her shoulder, “Express Yourself” has boldness and flair and visual confidence to burn. No wonder it heralded his arrival in such a big way.
3. Iggy Pop “Home”
 (1990)
Maybe the least well-known of Fincher’s run of incredible videos from 1990, this Iggy Pop outing sees Fincher go back to black-and-white basics, but such is Pop’s sheer charisma that it’s all you need. A great, unadorned, authentic rock’n’roll vibe whether Iggy’s writhing around on a graffiti’d bench or waging his eternal war on shirts —oh, and that little kick of the foot at the end is the best.
2. George Michael “Freedom ’90” 
 (1990)
Yeah, you may have heard of this one. A massive video for a massive hit, it manages to be both timeless, in the the way incredibly beautiful people are timeless, and totally of its time in its reflection of the early-90s obsession with the phenomenon of the supermodel. All wrapped up in what’s become pretty much an anthem of self-emancipation.
1. Madonna “Vogue” (1990)
The top spot could as easily have gone to “Freedom,” but I’m a fan of black and white, and Fincher’s mastery of it is unmistakable here. The sharp, directional lighting, the glowingly radiant skin tones, the sinuous grace of the bodies and costumes and of course the choreography that spawned an entire dance genre: it doesn’t get more iconic, more seminal, more Fincher, than “Vogue.”
