The red carpet at the Academy Awards is usually considered hallowed ground. Unlike the Grammys or the MTV Awards, or even the Golden Globes, it is neither the time nor the place for funny business. In fact, it is sometimes, as Sofia Coppola recently warned, too tasteful, too safe, and, sadly, too dull. But, in between the usual fishtail dresses and retro ballgowns, a few fearless women sometimes dare to really wow on the red carpet. There was Nicole Kidman in 1997, for example, spectacular in chartreuse by John Galliano for Dior. Then there was Marion Cotillard, redefining the meaning of fishtail gowns in Gaultier couture that actually looked like fish scales. Sharon Stone once turned a Gap button down into a power statement, and Lupita Nyong’o gave us princess dressing without being predictable. As for sheer bravado there’s always Cher, perpetually clad in Bob Mackie and eager to flout the conventions of “tasteful dressing.” Here, the 21 most memorable gowns of all time.