The Bojon Gourmet

1 Position a rack in the lower third of the oven, remove all other racks, and preheat to 350º.
Prepare the veg:
1 Cut the top off the pumpkin, leaving a large enough opening to get your hands in there and remove the gunk. Scrape out the strings and seeds - this can take a bit of effort, but it doesn't have to be perfect. (Reserve the seeds if you like; see headnote.) Set the pumpkin on a rimmed baking sheet or roasting pan.
2 Slice the white and light green parts of the leeks into 1/4" rounds, place the rounds in a large bowl, and fill with cool water. Swish the leeks around, separating the rounds, letting any dirt sink to the bottom.
3 In a large skillet, melt the butter and oil together over medium heat. Lift the leeks out of the water, shaking off excess water, and add them to the pan. Saute until wilted and tender, 10 minutes. Deglaze the pan with a splash of wine or stock, and season the leeks with a big pinch of salt.
Layer the components inside the pumpkin in the following order:
1 -1/3 of the bread cubes-half the cheese-half the leeks-half the sage-1/3 of the bread cubes-rest of cheese, leeks and sage-remaining 1/3 of bread cubes
2 In a large measuring pitcher, whisk together the half and half, eggs, black pepper, and 1 teaspoon of salt until thoroughly combined. Pour this mixture into the pumpkin. Add enough vegetable stock, if needed, to bring the liquid to 1 1/2 inches below the rim of the pumpkin (the liquid will bubble up, and the pumpkin will also release some moisture as it bakes).
3 Cover the hole with aluminum foil and cover with the pumpkin lid.
4 Bake the pumpkin until the flesh is tender (test this by poking the inside with the tines of a fork - they should slide in easily), about 1 1/2 - 2 hours. Remove the pumpkin. To serve, scoop portions of pudding and pumpkin out together. Garnish with a few small sage leaves if you like. Leftovers keep well in the fridge for up to 5 days. Reheat in an oven or toaster oven before serving.