For the chocolate-cherry pudding, heat most of the milk with whipped cream in a saucepan. Melt the chocolate in it and whisk the mixture until smooth.
Stir sugar, and cornstarch with the remaining milk until smooth and stir into the boiling milk while stirring fitfully with a whisk.
Continue to boil, stirring, for one to two minutes. Drizzle in rum and pour hot pudding into ramekins. Add cherries and let set.