Spend one hour drawing a Free Draw image. It's easiest if you make a mark, then wait for a few minutes, making sure your controller didn't shut itself off and making a new mark. Keep doing this until it unlocks. Thanks to Majinbro, you can save it and reload later and the time will count towards it. Thanks to MagicalChild, it is cumulative and he suggest not drawing a real picture, as it freezes your Xbox.