You can easily boost all 4 Drawful achievements in a single game. You will need at least 3 "players", and if you plan to boost this alone, it will be easiest with just 3. Find 3 phones, tablets, or PC web browsers, start up a Drawful game, and log everyone in. If you have a PC near to your Xbox it might be easiest to load up 3 different browsers (ie, firefox, chrome, safari, opera, whatever.) Personally i used a tablet for my "winner" player named X, and two phones for the "losers" named 1 & 2. Once you have this all set up just follow the instructions below.
With 3 players you will get 3 rounds, for a total of 9 "drawings" altogether, however you don't really have to draw anything. I wrote the initials of the title for each drawing, so if they wanted me to draw "People Boosting Xbox Achievements", i would just write the letters "PBXA". That way it will be very easy to remember the correct answers.
Make sure every turn your "winning" player gets the question right, and make sure your two "losing" players always pick the winner's fake answer, unless it's the winner's drawing, in which case they also pick the correct answer. I just wrote the fake answers as X for X and Q for 1 and W for 2 every time.
With only 3 players you only need to fool one player into picking your answer for:
On your winner's first turn, when the other players guess correctly you will earn:
At the end of the game, if your winner gets every question right you will get:
And finally the winner should win by a landslide, since they will be earning points for being right, for the other players getting their drawing right, and also for fooling the other players when it's not their drawing. This will trigger the last Drawful achievement
(this achievement):
This should only take about 10-20 minutes altogether at most. Keep in mind only one gamertag can trigger achievements at a time, so make sure you have selected the profile you want at the main menu screen.