Multiple locations, cheesyjanes.com
If the name is any indicator, this San Antonio staple doesn’t mess around when it comes to cheese. With the wallet-friendly price of $4.99, the Triple Grilled Cheese includes cheddar, Swiss and pepper jack topped with tomato and garnished with pickle slices. It’s the perfect no-frills, comfort food experience worth sitting down for (their food truck menu doesn’t include grilled cheese).
Best with: an order of hand-battered onion rings and a milkshake—choose from one of 15 flavors.
Lion & Rose British Restaurant & Pub
Multiple locations, thelionandrose.com
Ask one of the UK-born regulars at this British-themed neighborhood pub about “cheese on toast,” and they’ll tell you it’s better across the pond. Still, Lion & Rose does it justice with the Jester’s Grilled Cheese ($5.99). Cheddar, American and provolone combine with toasted sourdough and (optional) hickory-smoked bacon or black forest ham to create a greasy sammie that soaks up the alcohol, but won’t make you regret your late-night nomming. In a place where the chef proclaims, “the gooier, the better,” and the kitchen is open till midnight, you can’t go wrong.
Best with: a pint of the Krombacher Pils on tap for its full, citrus taste.
Boiler House Texas Grill & Wine Garden
312 Pearl Pkwy, (210) 354-4644, boilerhousesa.com
It’s a good thing the Cowboy Up Grilled Cheese Benny ($15) can only be found on the brunch menu (served Saturday and Sunday from 10 a.m.-3 p.m.) because a date with this sandwich requires commitment … and a fork. The triple-decker featuring brie, provolone and queso blanco, also comes with tomatoes, bacon, two soft poached eggs and house-candied jalapeno pork sausage. “Honestly, people have asked me if I was smoking when I came up with it,” Executive Chef Jeff White quips. “But I just wanted to do something big, something unexpected. And once you crack that egg yolk—forget about it.”
Best with: mimosa(s) of the orange or grapefruit variety.
Max’s Wine Dive
340 E Basse, (210) 444-9547, maxswinedive.com
If you’re a traditionalist who believes grilled cheese should be accompanied by a bowl of tomato soup and a great glass of wine, this is your place. Max’s serves up Gruyère, provolone, mozzarella and roasted red bell peppers on toasted artisan bread for $14.75. It also comes with crunchy parmesan and parsley-dusted potato chips. But if we’re being honest, the best part is definitely dunking it in the creamy tomato soup.
Best with: a glass of Shiraz (The Lucky Country comes recommended) or Malbec (try The Last Judgment).
Green Vegetarian Cuisine
Multiple locations, eatatgreen.com
Green is where you go when you want a sinfully good grilled cheese ($9) without the element of gluttony. Sandwiched between multi-grain bread, cheddar and American cheeses blend effortlessly with sundried tomatoes and basil straight from the restaurant’s outdoor garden. It’s 100 percent vegetarian and kosher and can be made vegan with Daiya dairy-free cheese. Go on Wednesdays and enjoy the popular special that includes tomato basil soup.
Best with: sweet potato fries, kale salad or quinoa tabbouleh.
Multiple locations, meltingpointtruck.com
The Melting Point food truck, which regularly sets up shop at The Block or The Point Park & Eats on the weekend, is for grilled cheese connoisseurs on the go. Recently voted as the number three food truck in the country by mobile-cuisine.com, Melting Point boasts eight sandwiches on their regular lineup: Favorites include The All Nighter, The Stamos and The Caprese. The Grill-Zilla promises to take a bite out of the competition with a cheesy concoction comprised of a hamburger patty, roasted poblano peppers, grilled onions and pepperjack cheese. Two classic grilled cheeses (American on Texas toast) serve as buns. Our guess? It will have you wishing they weren’t so hard to track down.
Best with: the Banana-Rama, a banana and Nutella combo on cinnamon chip bread topped with sugar.
Honorable mention: The Chubby Melt, a burger meets grilled cheese available at The Lost Bar. You’ll want to pack antacid.