This Achievement requires the purchase of the
JACK Pack 1 for You Don't Know Jack DLC in order to unlock. This DLC includes 10 additional episodes. The episodes can be played solo, local multiplayer, or online multiplayer and in any order without affecting whether the Achievement unlocks.
Playing the episodes solo takes roughly 15-20 minutes per episode, for a total of roughly 2.5 - 3 hours before they have all been completed. You do not need to guess the Wrong Answer of the Day for this Achievement, however if you guess them you will also unlock the following Achievement along the way:
Incurable Hoarder will unlock once the 10th prize is obtained, midway through the episode, but JACK Wrack will not unlock until the 10th episode is completed.