Cover the pumpkin with 1 inch of cold water in a large saucepan. Bring to a boil, then reduce to a simmer and cook until it is fork tender, 20 minutes.
Add oil to a small pot and heat over medium heat to 350 degrees F. Once oil is hot add the pumpkin seeds and fry until crispy and brown, about 4 minutes. Remove to a plate lined with a paper towel and sprinkle with 1 teaspoon brown sugar, a pinch pumpkin pie spice, and a little salt. Set aside to use as garnish.
In a small pot over low heat combine heavy cream and butter. Heat until hot but not simmering.
Drain the pumpkin in a colander, tossing to remove any excess water. Add the pumpkin back to the saucepan; add hot cream and butter and 1/4 cup brown sugar and mash to a uniform consistency with a potato masher or press through a spider. Season with salt and pepper. Give it a quick mix with a hand mixer to incorporate some air.
Transfer to serving bowl and garnish with a sprinkle of brown sugar, a pinch of pumpkin pie spice, pumpkin seeds and some chopped chives.
Series: Kelsey & Spike Cook
Episode: Mashed Potatoes (Ep. 1)