Get out 2 or 3 cookie sheets and line them with parchment paper or waxed paper. Very carefully twist the tops off of all the Oreos and set all of your little Oreo bits and pieces on the prepared cookie sheets. Don't crowd them. I'd do about 12 per sheet.
Using the end of a chopstick or a skewer, dig a little channel in the cream filling on each Oreo. If you start at the edge and gently work toward the middle (instead of starting in the center and moving outward), you won't randomly lose big chunks of filling.
Put your candy melts in a microwave-safe bowl. Melt them according to package directions.
Dip the end of a lollipop stick in candy and set it in one of the Oreo cream filling channels you dug in step 2. Gently push it all the way in and all the way down. Gently! If you push too hard, the Oreo will break.
. Take an Oreo top, spoon a tiny bit of candy onto the blank side (dime-sized at the most), flip it over, and put it back onto its mate.
Repeat steps 4 and 5 with the rest of the Oreos and sticks and let them sit until completely set.
If the candy melts need a quick reheat before moving on, microwave them again briefly.
Take an Oreo Pop and dip it in candy until it is completely covered. You might need to tilt your bowl and kind of roll or swish the Oreo Pop around to get it covered. Once it is completely covered, hold it parallel to the table and gently tap the stick against the side of the bowl so that the excess candy coating drips back into the bowl. If you make sure to hold the Oreo Pop flat while doing this, any unevenness on the front will smooth itself out.
Set the dipped Oreo Pop on it's back on one of the prepared cookie sheets and sprinkle with crushed candy canes. Allow to set.
Repeat steps with remaining Oreo Pops.
When they're all dry, they may be individually wrapped.