In mixer cream butter. Add pudding and heavy cream beat for 90 seconds, than add powdered sugar, cocoa powder and vanilla and beat till light and fluffy. I beat it for 10 minutes.
Spread a thin layer of filling on each cracker, lay a lollipop stick on one and top with another cracker that also has filling on it. Lay out on parchment lined cookie sheet and place in fridge for about 1 hour.
When your pops are nearly chilled an hour, melt chocolate over double boiler. Be careful not to get chocolate too hot. I use a melting pot as it keeps it at the right temperature.
Remove chilled pops from the fridge and dip each into the chocolate filling. Gently shake off excess chocolate. You can add decorations like colored sugar or sprinkles nonpareils at this point, but only if you want to, they taste just great by themselves. Put pops onto styrofoam block till the chocolate sets up.
Please note if your dipping chocolate is too hot it can cause your pops to slide off the sticks. If you don't have styrofoam you can lay your pops flat on a piece of parchment paper or wax paper. Have fun and enjoy!