Goto Sensei's Swag and equip the Ink Shadow, might as well equip the Calligraphy Brush and the Parchment Background for the other achievements from the Art Box DLC.
Play a game of arcade. Now the bananas won't show up among the other fruits, the bananas are actually the 3 different powers ups ( Frenzy, Double-Points and Freeze ) I'm pointing this out because some people even called them Corn Dogs
The achievement works cumulative, it took me 7 games to obtain but this can vary due to the randomness of the bananas. My guess is anywhere between 5-10 games