This can be gotten on your first day if you really grind. You need 16 awards/medals in the Trophy Cabinet.
Play your Talent Show and then head into the toy box. Work your way into unlocking each of the mini games. Sit and Pet Pounce have good GEM per time ratio. Just be warned that playing games multiple times makes all the GEMs worth 1.
Here is a list of all the awards. http://www.xbox360achievements.org/forum/showthread.php?t=30...
The achievement will pop when you've won your 16th.