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1
Get out two saucepans. In one, start your custard by combining cream, milk, cinnamon and star anise pods over medium-low heat. You really do not want this any higher because you just want your mixture to steam (this took about 12 minutes on my stove). In your second saucepan, add the Malbec, raspberries, and heat over medium. Once this gets bubbling, monitor heat to keep it at a consistent, but slow simmer, stirring occasionally and breaking up the berries. Continue cooking this mixture in this manner until you are ready to add it to the custard (step 4).
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2
Meanwhile, whisk your egg yolks in a medium bowl until combined. Add sugar and whisk vigorously until mixture is thick and pale. You can use a hand mixer, but it comes together quickly and easily with a whisk. Set bowl aside.
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3
Once your cream mixture is steaming, remove pan from heat. Stir and let mixture cool for a minute. Slowly temper your eggs by adding a small amount of the heated cream (a ladle is good for this) into the eggs and whisking quickly to combine. Pour tempered egg mixture into remaining cream, quickly whisking to combine. At this point, I could have really used a third arm, to scrape the remaining egg-sugar mixture from the bowl effortlessly. Having someone hold the bowl while you are trying to whisk the custard (to prevent scrambling the eggs) and scrape the bowl simultaneously is helpful. Return custard to heat and cook, stirring, until the custard coats the back of a spoon and will hold a line drawn with your finger, about 5 minutes.
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4
Carefully add wine-raspberry mixture to your custard. Stir to combine and then strain mixture through a fine meshed sieve into a large glass container (I used my quart Pyrex), pressing down on solids with a spatula. You should have about a quart of custard. Cool slightly and cover with plastic wrap. Transfer to the refrigerator for 6-8 hours, preferably overnight.
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5
When you are ready to make your wine scream, get your swirls ready. For the raspberry swirl, combine washed and drained raspberries (it is okay if they have a little water clinging to them), sugar and creme de cassis (or framboise or lemon juice) in a small saucepan. Get your mixture bubbling, breaking up fruit with a spatula. After 10-12 minutes, your mixture should still be loose, but also a little jammy. Strain through a small sieve into a small container with a lid, pressing down on seeds and scraping back and forth to get out all your jammy pulp. Scrape the pulp off the bottom of sieve into your container. Stir to combine. You should have about 2 ounces of raspberry swirl. Transfer to refrigerator to cool.
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6
Prepare chocolate swirl by placing in a glass bowl or Pyrex. If using a bar, cut into small pieces. Microwave for 10 seconds at a time until chocolate is glossy and just melted. Check between each time, stirring as it melts, to make sure your chocolate does not seize. Add canola oil, stir well to combine and set aside to cool completely.
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7
Pour your custard into your machine and process according to manufacturer's directions. When your ice cream is about the consistency of soft serve (20-25 minutes depending on your machine), carefully pour cooled, melted chocolate into machine. Allow mixture to churn for a bit more before shutting off.
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8
In a 1.5 quart airtight container, or two smaller containers, fill bottom third with ice cream. Spread an even layer of raspberry swirl. Repeat layering with remaining ice cream and raspberry swirl for two more layers of both. Freeze for at least 3 hours before enjoying. Enjoy!
