To quit this horrid act

OT: Coolest people ever

My brother has managed to keep me from thinking about this boring market this morning with a simple question: “Who’s the coolest person EVER in [select field of activity]?”. What’s important here isn’t the achievement of the person (because, for example, if it were about straight success Mandela would win the politics section hands down). No folks, what we’re talking about here is cool. Here’s what we have so far:

The coolest person EVER in music?
Him: Bob Marley
Me: Eddie Cochran

The coolest person EVER in politics?
Him: JFK
Me: Ernesto El Che Guevara

The coolest person EVER in sport?
Him: George Best
Me: Ayrton Senna

The coolest person EVER in art?
Him: Da Vinci
Me: Warhol

The coolest person EVER in cinema?
Him: Sean Connery
Me: David Lynch

The coolest person EVER in business?
Him: Alan Sugar
Me: Richard Branson

The coolest person EVER in literature?
Him: Plato
Me: Jack Kerouac

One thing  I’ve noticed is that all our answers are male. This troubles me slightly, because although it was fairly easy to think of cool or very cool women in most of the fields in question (Uma Thurman, Aretha Franklin, Dilma Rousseff, Danica Patrick, Marissa Mayer, etc), none of them got to be the coolest of their ilk. Why is that? Is it my own sexist bias, or are men destined to be cooler in absolute terms?
But aside from that male/female thing, where are we going wrong? Got any better suggestions?

UPDATE: Oh dear, what have I started? Plenty of suggestion (mail and twitter), but one that wins over the above comes from reader J, who points out that Miles Davis invented cool and the rest are just poseurs. He has a point.

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