The Challenge die is rolled at the start of each turn to change the way players must draw. The possible challenges are:
- Draw 2 pictures in less than 1 minute.
- Draw with your eyes closed.
- Draw a picture using only one line (you cannot lift your pencil).
- Draw with your off hand (righties use their left hand, and vice versa).
- Play with the regular rules

The Fun phrase cards have common phrases on them, but are more challenging to draw. On any turn, the Picturist (the person drawing) may choose to play one of the Fun Phrase cards instead of the regular cards. If the team guesses correctly, they may add two points to their next roll of the standard die.

A nice change of pace for those who like this classic drawing game.