Sometimes, there's an extremely specific thing I want to do in Illustrator that isn't a default function - that's when I turn to the internet, and - usually - find a script that fulfills my goal.
This time, I had a group of objects and a group of colors. I wanted to apply those colors to the objects at random, rather than hand-coloring each individual piece, or attempting to randomly select groups of objects to color.
Enter Random Swatches Fill, a script I found at Vector Boom. Using it is super easy. First, just move the .js file to Illustrator's Presets/en_US/scripts folder.
Then, create your group of objects, and select them all.
Then, select the colors you want to use. They have to be in your default swatch palette, so if you're using another color group, drag them over and select by holding Ctrl and clicking, or by hitting one, holding shift, and hitting one at the end of the sequence.
Then just go to File > Scripts > Random Swatches Fill. And presto! Randomly colored objects.
To grab the script for yourself, head over to Vector Boom's post.