This achievement isn't as bad as you might think. All you really need is a second controller and you're set. Now the achievement tracker is a bit weird in this game at the moment and achievements don't seem to pop when they're supposed to. To fix this problem with any other achievement, simply start a new level and it will unlock.
Get both your first and second into a game of Adventure Mode. Select the very first level, and with your main controller, run to the end.
You do not need to take your 2nd controller with you to the end, and you do not need to play 10 different levels. You can simply replay the first level over and over. To get your achievement progress to count, go to the main menu and wait about 5 seconds and it will go up. After you get 10, the achievement will pop. If it doesn't, return to the main menu.