2 large Ugly tomatoes, cored and halved
1 head garlic, top trimmed
1/2 teaspoon liquid smoke
1/2 cup (+4 tablespoons) olive oil, divided
Kosher salt and ground black pepper
1 bunch cilantro, leaves picked
1 bunch Italian parsley, leaves picked
1 lemon, zested and juiced
1 lime, zested and juiced
4 portabella mushroom caps, gills removed
Parmigiano Reggiano, for garnish
Extra-virgin olive oil, for garnish
DirectionsPreheat oven to 350°F. Preheat grill on high.
Toss tomatoes, garlic, and jalapeño with liquid smoke, 2 tablespoons oil, salt, and pepper in a medium mixing bowl. Spread tomatoes, cut side down, and jalapeño onto parchment-lined sheet pan; wrap garlic in foil. Place sheet pan and wrapped garlic into oven; cook until skin of tomatoes and jalapeño are blistered and garlic is soft, about 25–30 minutes. Let cool 10 minutes.
Peel skin from tomatoes; place into food processor. Peel skin and remove seed pod from jalapeño; place into food processor. Squeeze garlic from head into food processor; add cilantro, parsley, zest, and juices. Pulse until paste is formed; with processor running, drizzle in 1/2 cup olive oil until fully incorporated. Season with salt and pepper to taste.
Lay mushroom caps onto parchment-lined sheet pan; drizzle with remaining 2 tablespoons oil and season with salt and pepper. Place on grill; cook until lightly charred with marks, rotating 45 degrees after 1 minute, about 2–3 minutes. Flip and cook until caps are softened, about 2–3 minutes more. Remove from grill and leave cool 2 minutes.
Place a few spoonfuls of chimichurri onto each of 4 plates; spread with back of spoon over plate. Cut mushroom caps into 1/2-inch strips; stack in center of plate. Shave parmesan with a peeler over top of mushroom strips. Drizzle with extra-virgin olive oil.