Hilary Swank, 2000 Oscars
Hilary Swank’s leading performance in “Boys Don’t Cry” was a win, but her hair just didn’t make the cut at the 2000 Oscars. It’s so drab and reminiscent of a total boy cut. It also makes her forehead look huge. In fact, I even had to type in “Hilary Swank’s forehead” into Google to see if it’s an optical illusion, or if it’s really that large. Turns out, bangs + lots of teasing + a large forehead = totally unflattering.