Edit, Came back to play the game properly in early 2017 and the community levels server wasn't always available. If you can't connect you'll have to play the game to grab the achievement.
Select Community Levels, Sort by Newest and select TA SP (searching will also work (Filter then Phrase).
Once the level has loaded, point the right stick up
so that the directional arc is directly above you then tap
to throw the Inflate-a-mate then press
to embiggen it. The Inflate-a-mate will land on your head and kill you and the achievement will pop.
If you haven't completed the Connoisseur Club achievement go on to hack the terminal that is next to the exit (press and hold
) and walk into the exit then rate it. *pop*