Place ice-pop mold in freezer and 10 pop sticks in a bowl of warm water.
Peel bananas, break each into several pieces and place in a food processor with sugar, juice and vanilla. Blend until very smooth. Divide mixture among molds. Poke fruit with a skewer a few times and tap bottom of mold on counter to release air bubbles.
Place lid on top and insert pop sticks. Freeze for 8 to 12 hours. After you remove pops, drizzle with chocolate syrup. Let set for 30 seconds before serving.