Preheat oven to 350°F. Grease or line two large baking sheets.
In a large bowl with an electric mixer, beat butter, oil, and sugar until fluffy, about 4-5 minutes. Add egg and vanilla, and beat an additional 2 minutes.
In a large mixing bowl, whisk flour and baking soda to combine. Stir into butter mixture until thoroughly combined. Fold in cherries and chocolate chips.
Drop the dough (1 heaping tbs. per cookie) onto the prepared baking sheets (about 3″ apart). Bake cookies until firm, about 12-14 minutes. Transfer cookies to a wire rack to cool.
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