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In one medium size bowl, add 1 ½ cups of milk and chocolate pudding mix. Whisk for 2 minutes. Set aside. In a second medium size bowl, add remaining 1 ½ cups of milk and vanilla pudding mix. Whisk for 2 minutes.
To assemble, layer popsicle well with chocolate, brownies, cherries and vanilla pudding. Repeat until all wells are filled.
Transfer to freezer and let set, about 6 hours or overnight (freezing time will vary depending on freezer setting and how full your freezer is).