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Jaeger-LeCoultre Gyrotourbillon 1 – $400,000

This watch is clearly complicated, but it has a feature some of the others don’t, a tourbillon. What’s a tourbillon? A wrist-mounted anti-gravity device. Tourbillons (in the most basic terms) prevent gravity from adversely affecting accuracy. Normal tourbillons only rock one-axis anti-gravity, this tourbillon rocks two. No word yet on when the third and fourth axis will be integrated.

Rolex Submariner – $234,000

At some point in time, everyone has held, worn, or owned a Rolex Submariner. This one is special because it was held, worn, and owned by the one and only Steve McQueen. That’s right, the “King of Cool” owned this particular submersible, self-winding, stainless steel oyster bracelet Rolex. You’re getting time, Rolex, and bona fide badassery.

Vacheron Tour de l’Ile – $1,250,000

Vacheron is the oldest watch manufacturer still in existence since its inception in 1755. 250+ years of history allows them to make watches that eclipse most others. The Tour de l’Ile has tourbillon, two faces, and more complications and parts than even the Breguet Marie Antoinette (hopefully without the beheading) making it the most complicated serial wrist watch ever made. It’s worth JUST shy of a Veyron… unless you buy used.

AP Royal Oak Grande Complication – $560,000

Audemars Piquet (that’s where the AP comes from obviously) does it again with the Royal Oak Grande Complication. The Grande Complication is another watch that has a perpetual calendar accurate until long after you will no longer be alive. It has a lot of the same complications as the other watches (minute repeater, split seconds chronograph, aforementioned perpetual calendar) but presents them in a way that doesn’t require a thousand page instruction manual just to read. Real men don’t use instruction manuals.

Richard Mille Tourbillon – $525,000

Look at it. It looks like a Rube Goldberg machine had sex with the Gugenheim and the offspring was skeletonized. Quite a few of these watches have modern elements, but none of them have the modern design that this watch does. Made of aluminum, titanium, and awesome it would be the perfect compliment for the new clear hood you just put on the Ferrari.