Today’s Eggplant Parm Grilled Cheese should only be attempted on a rainy, miserable day. You know, a day when you simply can’t weather the weather (Ugh! I’m terrible). I mean, smooshing fried goodness into a gooey cheese-riddle sandwich is not the kind of behavior you can justify on a daily basis. No, this sandwich should be reserved for smash-the-glass style emergencies. It should be applied when the sky looks set to destroy you, your pant legs are soaked, and your mood is so low it’s in your shoes. This sandwich has the ability to restore your faith in humanity. It has the power to make you enjoy the sting in your frosty cheeks and fingers. It has the capacity to make you love inclement weather just because it feels so good to escape it. Yes, this Eggplant Parm Grilled Cheese is *that* powerful, so it’s best to respect it.
I’m totally kidding! It’s a frickin’ sandwich, there’s no need to build a religion around it. But one thing I will say about this Eggplant Parm Grilled Cheese is: Do not indulge in it too frequently or it will lose its restorative properties. Yes, like most potent feel-good drugs, you will eventually form a full-blown dependency. And this is not just a bad thing because of the amount you will spend on cheese, it’s a bad thing because the sandwich won’t be special anymore. It won’t be what you crave when your world is crumbling. It won’t be that easy win when you’ve done nothing but lose for 24 hours. You have to respect the meals that give you that boost and not abuse them.
If I sound earnest, it’s because I think I’ve found my sandwich. I mean, there have been other sandwiches in my life. The fried egg sandwich and I had a good ten years together. But I was clingy. I asked too much of it. I invited it to too many meals and I finally got sick of it. Yes, like the raspberry vodka of my youth, I can no longer contemplate partaking in my once beloved sandwich. Although, oddly enough, I’m still about breakfast tacos that essentially have all the same components but with salsa. I can’t wait to see how that one will end. This is a weird post. Why am I writing about this? Whatever. Let’s keep going.
So yeah, I really really love this Eggplant Parm Grilled Cheese, which surprised me because I’m not so much about the eggplant. When I was 20, I came down with the worst stomach flu and one of the last things I ate before being struck down was baba ganoush. Although my susceptibility to a stomach bug had nothing to do with the baba ganoush, it was guilty by association and to this day I never touch the stuff. And for a long time, this distaste for baba ganoush extended to eggplant everything.
It was green curry that brought me back to the fold. I flipping love the eggplant chunks in green curry, mostly because they’re basically sponges soaked in spicy coconut curry goodness. Really, it’s no surprise that the first eggplant recipe on this blog features green curry paste. Eventually, I moved onto eggplant parmesan and that seemed to go alright, so I sort of considered myself cured. Today, I’m not necessarily enthusiastic about eggplant (although, I’ve always loved the color) but there are dishes where I really like it.
So, I planned out this Eggplant Parm Grilled Cheese because I generally like parm sandwiches, be they chicken or beanball. But now, I’m like chicken parm who? This Eggplant Parm Grilled Cheese is the bee’s-f*cking-knees. It’s so good! The eggplant retains it’s crispiness while the cheese goes into a full gooey melt. And when you load it up with a good, quick marinara, you don’t need tomato soup on the side. Honestly, you can add the grilled cheese’s natural companion if you want, I’m just saying the sandwich is very a much a meal in-and-of-itself. Not here to soup shame anyone.
This Eggplant Parm Grilled Cheese is the perfect respite from stupid coworkers, volatile drivers, and frigid lakes of rainwater. It’s exactly what you need as temperatures get colder and the reality of winter starts to creep in. So, go forth and fall in love with this sandwich, for keeps.
- 1 eggplant, cut into medallions
- 1 1/2 teaspoon salt, divided
- 1 cup all-purpose flour
- 2 eggs, lightly beaten
- 1 1/2 cups whole wheat breadcrumbs
- 1 cup grated Parmesan, divided
- 1/4 cup canola oil
- 8 slices sandwich bread
- 1 batch Simple Marinara (see below)
- 1 (340g/12oz) mozzarella ball, sliced
- 2 tablespoons butter
- Handful of fresh basil leaves
- 1 tablespoon olive oil
- 1 sweet onion, finely diced
- 4 cloves garlic, minced
- 3/4 cup white wine, divided
- 1 can whole tomatoes
- 1 teaspoon salt
- 2 teaspoons demerara sugar
- 1 teaspoon dried oregano
- 1/2 teaspoon crushed red pepper flakes
- 1/4 cup fresh basil, chiffonade
- Heat the olive oil in a large deep skillet until shimmering. Add the onion and saute until just translucent, about 3-5 minutes.
- Add the garlic to the onions and saute until fragrant, about 2-3 minutes.
- Pour in the white wine and deglaze the pan.
- Stir in the tomatoes and mash them slightly with the back of a wooden spoon.
- Add the salt, sugar, dried oregano and red pepper flakes and stir until combined.
- Bring the mixture to a boil, then reduce to a gentle simmer. Cover and let cook for 20-25 minutes or until the sauce reaches a jammy consistency. If the sauce gets too thick, stir in a little extra wine or stock.
- Remove the sauce from the heat and stir in the basil.
- Puree the sauce using an immersion blender until it reaches the desired consistency - I left mine kind of chunky.
- Set the sauce aside to cool until ready to use. If making ahead, let the sauce reach room temperature before transferring it to a resealable container. Store the sauce in the fridge for up to three days.
- Place the eggplant on a baking sheet lined with paper towels. Using 1 teaspoon of the salt, liberally salt both sides of each eggplant medallion. Let the eggplant sit for 40 minutes.
- Wipe the excess salt and moisture from the eggplant and set aside.
- Place the flour, eggs and breadcrumbs in separate bowls. Stir 1/2 cup of the Parmesan cheese and the remaining salt in with the breadcrumbs.
- Take a piece of eggplant and dip it first in the flour then the egg then the breadcrumb mixture. Set the breaded eggplant piece on a baking sheet and repeat until you run out of eggplant.
- Pour the canola oil in a large cast iron skillet. Place the skillet over medium heat and heat the oil until shimmering.
- Working in batches, fry the eggplant in the skillet for roughly 3 minutes a side or until golden brown.
- Transfer the fried eggplant to a large plate lined with paper towel.
- Butter 1 side of each of the slices of bread and place them on a baking sheet, butter-side-down.
- Spread 2-3 tablespoons worth of the marinara sauce on each slice of bread.
- On half of slices of bread, top the sauce with 3 slices of mozzarella.
- Top the mozzarella with 3 fried eggplant medallions followed by 3 more slices of mozzarella.
- Sprinkle the mozzarella with the remaining Parmesan and finish with 4-5 fresh basil leaves.
- Place the sauce-only slices on top of the stacked slices.
- Wipe the cast iron skillet of excess oil and place over medium-low heat.
- Fry the sandwiches, two at a time, until the cheese melts and the bread is golden brown, about 5-7 minutes a side. Make sure the heat isn't too high or the bread will burn before the cheese melts.
- Place the sandwiches on a plate and place the plate in 150F oven to keep them warm before moving onto the remaining sandwiches.
- Serve the sandwiches immediately with additional marinara sauce for dipping.