The Metropolitan Museum of Art’s Costume Institute Gala, otherwise known as the Met Gala, might be the most-watched red carpet on earth. Some of it has to do with watching A-listers from every walk of life (movies, music, high society) in the same place. But most of it has to do with seeing how guests attack—or demure from—a given year’s theme.

In years past, most famous guys (or, more accurately, their stylists) have done right by the black tie (or, on occasion, white tie) dress code by playing it safe. But thanks to history’s pioneering menswear mavericks, men’s celebrity fashion has shifted gears these last few years, which has propelled more and more famous dudes to really go there on the red carpet…especially when the Met Gala gives them carte blanche to do so. That said, let’s also pour one out for the guys who either don’t care, or care too much, that their Met Gala fits defy dress code, convention, and sometimes description. (Armor? Robot arms? Robot armor arms?)

Let’s take a look back at the guys who have honored the night’s fashion-first ethos through the years:

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