Slow-Cooked Collard Greens in Olive Oil
['1/2 cup extra-virgin olive oil, plus more for drizzling', '8 garlic cloves, thinly sliced', '1/2 teaspoon crushed red pepper flakes', '2 bunches collard greens, ribs and stems removed, leaves torn into 2" pieces', 'Kosher salt', '1 tablespoon (or more) apple cider vinegar', 'Generous pinch of sugar']
Heat 1/2 cup oil in a large saucepan over medium. Cook garlic and red pepper flakes, stirring often, until garlic is golden, about 4 minutes.
Add collard greens to saucepan a handful at a time, stirring until each addition is wilted before adding the next. Season with salt and add 1 cup water. Bring to a simmer, then reduce heat so mixture is at a very gentle simmer. Cover and cook, occasionally removing lid to stir, until greens are tender and very dark green, 1–1 1/2 hours.
Let cool slightly, then stir vinegar and sugar into greens. Transfer to a serving bowl and drizzle with more oil and a splash more of vinegar if desired.
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