Preheat your oven and slice the top off the head of garlic to expose the cloves.
Drizzle the garlic with olive oil, wrap it tightly in foil, and roast for 35 to 40 minutes, or until the cloves are soft and golden.
Allow the garlic to cool slightly. Squeeze the roasted cloves into a bowl and mash them into a smooth paste.
Add the water, pineapple juice, teriyaki sauce, soy sauce, dark brown sugar, lemon juice, minced onion, roasted garlic paste, and 1 tablespoon of Jack Daniel’s Whiskey to a medium saucepan.
Bring the mixture to a gentle boil over medium heat, stirring until the brown sugar has completely dissolved.
Reduce the heat to low and simmer for 20 to 30 minutes, stirring occasionally, until the sauce has reduced by about one-third and begins to thicken.
Stir in the crushed pineapple and the remaining Jack Daniel’s Whiskey.
Simmer for another 2 to 3 minutes, just long enough to warm everything through without cooking off all the fresh whiskey flavor.
For an ultra-smooth glaze, blend the sauce with an immersion blender or carefully transfer it to a standard blender and blend until smooth.
Brush the glaze onto chicken, ribs, pork chops, salmon, burgers, or smoked pork loin during the final 10 to 15 minutes of cooking. This helps prevent the sugars from burning.
For a thicker and stickier glaze, allow the sauce to simmer a little longer.
Store in an airtight container in the refrigerator for up to 2 weeks. The flavor improves after resting overnight.