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Wash and dry the cherries. Remove the stems and pits, then slice them in half.
Add the cherries and sugar to a saucepan. Cook over medium-low heat for about 10 minutes, stirring occasionally. The cherries should soften slightly while still keeping their shape, and the juices should thicken. Remove from the heat and let cool completely (refrigerate to speed up cooling).
In a large bowl, whip the heavy cream with the vanilla extract until almost stiff peaks form.
Add the sweetened condensed milk and cold cream cheese. Mix with a hand mixer just until combined. Leave a few small chunks of cream cheese for that classic cheesecake texture.
Pour half of the ice cream mixture into a freezer-safe container. Spoon over half of the cherry mixture and sprinkle with half of the crushed vanilla wafers. Gently swirl.
Repeat with the remaining ice cream mixture, cherries, and vanilla wafers. Swirl lightly to create a beautiful ribbon effect.
Cover and freeze for 8–12 hours, or overnight, until firm.
Scoop, serve, and enjoy every creamy, cherry-filled bite!