This can be accomplished in a 3-player game. In round 1, put "NO" as the answer for both quips for player 1. Put anything else for players 2 and 3. When voting, don't vote for "NO". Player 1 will be in last place after round 1.
Put "YES" for both quips in round 2 for player 1. Put anything else for the other two players. Make sure to vote for "YES" during the voting. In round 2, points are doubled, so player 1 will now be in the lead.
During round 3, put "YES" for player 1, and "NO" for players 2 and 3. Just make sure to again vote for "YES", and vote for Schmitty's answer if it is against one of the "NO" answers, for good measure.
The achievement will pop after the game ends.