1Pour 2 tablespoons vodka in circle in center of small plate. Turn martini glass upside down and dip rim of glass in vodka, spinning back and forth until coated. Repeat with 4 more martini glasses.
2In center of another small plate, sprinkle sugar and red pepper. Turn each martini glass upside down and dip rim of glass in mixture, spinning back and forth until coated.
3Drizzle chocolate syrup inside glasses, forming swirling design. Place glasses in freezer.
4Fill shaker with ice; add liqueur, 1 cup vodka and the half-and-half. Shake well. Remove glasses from freezer. Strain mixture into glasses and serve.