Preheat oven to 425°F and line a baking sheet with foil; oil lightly. Toss wings with salt, pepper, and oil, then arrange in a single layer.
Roast wings 35–40 minutes, flipping once, until skin is crisp and juices run clear.
Meanwhile, combine pineapple juice, soy sauce, brown sugar, rice vinegar, garlic, and ginger in a saucepan over medium heat.
Simmer 6–8 minutes, then stir in crushed pineapple. Whisk cornstarch slurry and add, cooking until sauce thickens, about 1–2 minutes.
Toss roasted wings in the teriyaki-pineapple sauce to coat. Return to oven 3–5 minutes to caramelize slightly.
Sprinkle with sliced green onions and sesame seeds before serving.