We love the look of 1950s-style pineapple-glazed ham, maraschino cherries and all, but not the cloying sweetness. We spiked the glaze for our retro-chic version with hot sauce and apple cider vinegar to cut through the sugar. For the best results, the ham should rest before slicing just like any other roast; a full hour is ideal, but 30 minutes will work.
- ½ pineapple, peeled, sliced into rings
- 1 large orange, sliced into thick rounds
- 1 10-lb. cured smoked bone-in ham or 6-lb. cured boneless ham
- ½ cup apple cider vinegar
- ½ cup (packed) light brown sugar
- Maraschino cherries (for serving)
Preheat oven to 300°. Stack 2–3 sheets of foil ample enough to cover ham on a work surface and arrange pineapple and orange slices on top in a single layer. Set ham on fruit (if using a bone-in ham and it has a fat cap, score very lightly, making cuts about ¾" apart) and wrap up tightly. Transfer to a wire rack set inside a large rimmed baking sheet and bake until an instant-read thermometer inserted into the thickest part of ham registers 115°, 3–3½ hours for boneless, 3½–4 hours for bone-in.
Meanwhile, bring pineapple juice, vinegar, brown sugar, and hot sauce to a boil in a large saucepan. Reduce heat; simmer, swirling occasionally, until thick enough to coat a spoon. Keep warm.
Remove ham from oven and increase oven temperature to 425°. Unwrap ham, peeling back the foil so it covers the baking sheet (this will make for easy cleanup). Once oven is at 425°, baste ham with warm glaze and return to oven. Bake, brushing with more glaze every 3 minutes or so, until glaze is deeply browned and thermometer registers 125°, 12–15 minutes. Carefully transfer ham to a cutting board and let rest 30–60 minutes before slicing.
While ham is resting, roast fruit, spooning juices over from time to time, until deeply browned, 20–25 minutes.
Serve ham with roasted fruit and cherries alongside.