The Jackbox Party Pack 10 (UP)

Start a 4 player Tee K.O. game. Go through the drawing and slogans. Then when it comes to vote on shirts have players 1 & 2 vote for 1 shirt, and players 3 & 4 vote for the other shirt. This causes a tiebreaker, and the tiebreaker is an arbitrary difference (things like shortest slogan, or longest slogan, or shortest time to draw, etc).

Keep repeating creating ties like this until there's one player who wins a tiebreaker twice in the same game, achievement pops right away.