Just looking for new ideas for Christmas.
I have two. One is for the sort you probably grew up eating made with cocoa powder and more sugar. The other is made with 62% chocolate, less sugar and is probably a bit more refined.
I’ll post 'em both and you can decide.
Chocolate Pudding Like Mom Used to Make
Mix the following dry ingredients together in a saucepan:
1/2 Cup Hershey’s cocoa powder
1 cup sugar or less, to taste
1/3 cup cornstarch
1 tsp salt or less, to taste
Pour in:
3 cups whole milk
Stir milk into mixed dry ingredients in saucepan. Cook over medium heat and stir till thick. Cook for 2 minutes longer at a boil.
ETA:
Then add:
3 TB butter
1 1/2 tsp vanilla
Remove from heat, add butter and vanilla. Pour into prepared pie crust or individual serving bowls. Cover each with cling film to avoid pudding skin.
Refrigerate till firm, between 4-6 hours.
Serves 6.
Silky Chocolate Pudding
Dry ingredients:
1/4 cup cornstarch
1/2 cup sugar
1/8 teaspoon salt
Add:
3 cups whole milk
Stir in:
6 ounces 62% semisweet chocolate, coarsely chopped (I used good quality semisweet chocolate chips; use 70% bittersweet if you want more of a dark chocolate kick)
1 teaspoon pure vanilla extract
Combine the cornstarch, sugar and salt in the top of a double boiler. Slowly whisk in the milk, scraping the bottom and sides with a heatproof spatula to incorporate the dry ingredients. Place over gently simmering water and stir occasionally, scraping the bottom and sides. Use a whisk as necessary should lumps begin to form. After 15 to 20 minutes, when the mixture begins to thicken and coats the back of the spoon, add the chocolate. Continue stirring for about 2 to 4 minutes, or until the pudding is smooth and thickened. Remove from the heat and stir in the vanilla.
Strain through a fine-mesh strainer (or skip this step if you’re a slacker like me) into a serving bowl or into a large measuring cup with a spout and pour into individual serving dishes.
Again, cover with plastic wrap unless you like pudding skin.
Refrigerate for at least 30 minutes and up to 3 days.
How rich do you want to go?
Martha Stewart’s recipe has worked well for me.
I much prefer chocolate pudding that has egg in it. Here’s a good standard recipe. If you feel fancy, you can sub half & half (or cream) for part or all of the milk for extra decadence.
And don’t forget about the heavenly dessert that is butterscotch pudding. I knew of a restaurant whose signature dessert was butterscotch pudding made with cream, dark muscovado sugar, egg yolks, and 8-year-old scotch.
Damn, now I’m hungry.
If you don’t want a custard style such as @needscoffee posted, a ‘quick’ option is to make an instant pudding powder based on Alton Brown’s well regarded one:
Since when cooking you use both milk and heavy cream, it’s pretty darn rich, even if the base is a homemade powder, and it’s quality increases as the quality of the ingredients does. So this is a good place to use a solid Dutch Process Cocoa powder, not just Hershey.
For a Mexican twist, add a small pinch of good quality cayenne pepper and Ceylon cinnamon, and you’ll be in heaven.
If a spoon and an unlimited amount of that pudding was put in front of me, I’m pretty sure I would eat myself to death, and die happy.
I always thought the skin was the best part. We poured some milk on the pudding, and the contrast between the sweet pudding and the…hmmm… Clean-tasting milk was always a joy.
I don’t think I’ve had chocolate pudding for many many years, though.
Same here!
It’s all what you’re raised with, I suppose. 
I’ve been making homemade chocolate pudding since I was about 9. The way I was taught, pudding skin was to be avoided at all costs! So that’s how I did it and how I learned to like it.
I imagine if I’d been taught to make pudding with skin, it would be my favorite thing, too.
I have long since lost my butterscotch recipe but no lie, people said it was the best they every had.
I’ll bet! Most of us have never experienced homemade butterscotch pudding. Even the most basic recipe is heads-and-shoulders above store-bought. I’ll bet yours was delicious.
More of a steamed, cakey chocolate pudding. Really good. Barbara Kafka's steamed chocolate pudding
Another vote for this—and this thread has reminded me that it’s been way too long since I’ve had skinney pudding.
(When I’ve made it myself, I’ve only ever used the basic pudding mix that comes in a box. The first time I tried making pudding on the stove, I burned it and found the whole process to be a PITA. The next time, I did it in the microwave and found it much easier.)
How much butter and vanilla? Thanks!
The amounts of butter and vanilla were left out of your first recipe.
Oh! How silly of me.
3 TB butter
1 1/2 tsp vanilla extract
Sorry about that!
Thanks! Now I have Sunday planned. 
Thanks! I’m not good at guessing, especially when it comes to butter. The more butter the merrier!
LOL, me, too.
That’s always been my motto!