Preheat oven to 350° F. Grease a 9" springform pan. Set aside.
In a large heatproof bowl, melt the chocolate and butter in the microwave on 30-seconds burst, stirring after each burst.
Add sugar and salt. Stir to combine.
Add eggs, vanilla extract, and chocolate extract (see note). Stir to combine. Add flour, and mix until just incorporated.
Scrape the brownie batter into the prepared pan. Bake about 20 minutes, or until a toothpick inserted in the center comes out clean. Do not overbake! Allow brownie to cool completely.
For Cheesecake:
In a small bowl, sprinkle gelatin in an even layer over the top of the water. Allow to set 5 minutes to soften.
Once softened, place the juice/gelatin mixture in the microwave for about 10 seconds to warm, and stir until the gelatin is dissolved and the mixture is smooth. Set aside to cool to room temperature.
In the bowl of a stand mixer, combine cream cheese and sugar. Beat until combined and smooth. Scrape down the sides of the bowl. Add gelatin mixture and peppermint extract and mix to combine. Scrape down the sides of the bowl again. Once fully incorporated, set aside.
In another mixer bowl, use the whisk attachment to beat the cream and powdered sugar to soft peaks. Gently fold the whipped cream into the cream cheese mixture in three additions, being careful not to deflate the mixture.
Gently fold in crushed candy canes. Avoid overmixing, as mixture could deflate, and mixing will cause the red color to run.
Spread the cheesecake onto the cookie dough layer. Chill in the refrigerator at least 4 hours.
For Whipped Cream:
Place cold heavy cream, powdered sugar, and vanilla bean paste (see note) in the bowl of a stand mixer. Start the mixer on low speed, and gradually increase the speed to high. Whip until the cream thickens and forms peaks.
Spread or pipe the whipped cream on top of the cheesecake as desired. Sprinkle crushed candy canes over the top, if desired.Enjoy!
Notes
Note on chocolate extract: I highly recommend this (sometimes overlooked) extract! It lends amazing depth of flavor to chocolate baked goods! If you can't find it in your local grocery store, you can find some [here]. Even better, make yourself some [Homemade Chocolate Extract] for next time!
Note on vanilla bean paste: You know me, it's in everything! Delicious and more economical than whole vanilla beans, this ingredient is my go-to for an extra punch of flavor. You can find it online [here]. If you prefer to substitute, you can use an equal measure of vanilla extract.