It's where actresses often take a risk and not care about what might get them on the best dressed list. Instead some chose to wear something that challenges the notion of what is red carpet fashion, perfectly reflects a moment in time or is perhaps a more authentic reflection of their personality. And it's often these looks that stand out the most in our collective memories, both in a "Yas, queen!" way and a "Hmm...we're not quite sure about that" way.
Sometimes, celebs are paying homage to bygone eras, but the cuts just don't quite work today. That's precisely what happened with the odd shoulder ruffles on Nicole Kidman's sequined Alexander McQueen gown last year...
...as well as the vintage aqua Travilla dress that a 1960s screen siren would've loved, but didn't quite work on Lana Del Rey in 2015.
Another common theme on this list: great look, wrong venue. As much as we love Whoopi Goldberg, this yellow ensemble (sweatsocks included!) she topped with a white cardigan in 1986 was more fitting for the gym than the Globes.
Keri Russell was ready to hit the beach in 1999.
Lara Flynn Boyle was literally a ballerina in 2003.
And Diane Kruger looked ready to cosplay Princess Jasmine in 2005.
But our favorite strange looks of all may be the very punk choices made by Sharon Stone in 2003 and Courtney Love in 2000.
There have been other wild choices made by celebs attending the Globes over the years. See them all in the gallery below: