This is a lazy afternoon favorite. Not too long ago we were visiting Portland (Oregon, not Maine) and stopped at one of their famed Food Carts. This is a distillation of one of the sandwiches we had there, with some twists learned from other grilled cheese attempts throughout the years and found online. Using mayonnaise on the outside of the sandwich instead of butter gives a better crust and is less prone to burning. In addition, having patience on a lower heat also allows the cheese to melt without the outside crust turning black.
For a single sandwich (multiply as needed) you’ll need x2 large slices of sourdough bread, 8 oz of sharp cheddar cheese (thinly sliced), 1/2 large onion (thinly sliced), 4 or 5 large ripe figs (stems cut off and sliced into quarters), olive oil, 1 Tbsp unsalted butter, balsamic vinegar, mayonnaise.
Pre-heat the oven to 350.
In a skillet heat 1Tbsp olive oil and 1 Tbsp unsalted butter until butter is melted – use medium high heat and don’t let it burn or brown. Add the sliced onion and figs and bring the heat down slightly – to medium. Make sure everything is evenly spread out in a single layer and let simmer without stirring for about 4 mins. Gently stir once around and let whole thing simmer again for another 2-3 mins until browned. Turn up the heat slightly and add 1 Tbsp balsamic vinegar and stir well until the vinegar has evaporated. Remove the onions and figs from the skillet with a slotted spoon or spatula into a bowl leaving the oil/butter residue in the skillet.
Place the sliced cheese on both halves of the bread, then add the onions and figs, on top of the cheese layer on one side only. Carefully place the other bread slice, with the cheese layer, on top of the first slice with the cheese, onion and figs.
Spread about 1 Tbsp mayonnaise evenly on the top slice and place the whole sandwich, mayo-slice-side down back into the skillet (if you need a little more butter or oil before returning the sandwich to the skillet, please add). Keep the heat at medium – max.
Spread another Tbsp of mayo on the slice side that is up in the skillet and cook over medium heat (don’t turn it up too high) for about 3-4 mins per side – until golden.
As a final touch – place the whole skillet into the pre-heated oven for about 3-5 mins just to complete the cheese melting process.
Serve sliced and hot.