Challah Grilled Cheese

Challah Grilled Cheese

Challah Grilled Cheese, Eat Something by Evan Bloom & Rachel Levin, Photography by Maren Caruso.

Eat Something by Evan Bloom & Rachel LevinThis long-awaited cookbook (the first one for Wise Sons!) is packed with homey recipes and relatable humour; it is as much a delicious, lighthearted, and nostalgic cookbook as it is a lively celebration of Jewish culture.

Stemming from the thesis that Jews eat by occasion (and with enthusiasm), the book is organized into 19 different events and celebrations chronicling a Jewish life in food, from bris to shivah, and all the makeshift and meaningful events in between, including: Shabbat, Passover, the high holidays, first meal home from college, J-dating, wedding, and more.

• Both a Jewish humour book and a cookbook
• Recipes are drawn from the menus of their beloved Bay Area restaurants, as well as all the occasions when Jews gather around the table.
• Includes short essays, illustrations, memorabilia, and stylish plated food photography.

Wise Sons is a nationally recognized deli and Jewish food brand with a unique Bay Area ethos—inspired by the past but entirely contemporary, they make traditional Jewish foods California-style with great ingredients.

Recipes include Braided Challah, Big Macher Burger, Wise Sons’ Brisket, Carrot Tzimmes, and Morning After Matzoquiles, while essays include Confessions of a First-Time Seder Host, So, You Didn’t Marry a Jew, and Iconic Chinese Restaurants, As Chosen by the Chosen People.

• The perfect gift for Wise Sons fans of all ages, lovers of Jewish food and humour, as well as gift-givers young and old looking for Jewish-themed gifts for bar mitzvahs, birthdays, weddings, and more
• Great for those who enjoyed Zahav: A World of Israeli Cooking by Michael Solomonov, The 100 Most Jewish Foods: A Highly Debatable List by Alana Newhouse, and Russ & Daughters: Reflections and Recipes from the House That Herring Built by Mark Russ Federman
• A must for anyone looking to expand their knowledge of Jewish cuisine and culture

Eat Something: A Wise Sons Cookbook for Jews Who Like Food and Food Lovers Who Like Jews (Jewish Food Cookbook, Recipes for Jewish Holidays) is available at an

Challah Grilled Cheese

Grilled cheese is the ultimate comfort food, but challah grilled cheese is heavenly. In our opinion, no other bread will do. We like the high-low combination of American cheese and Gruyère. The American cheese provides a perfect melty texture, and the Gruyère adds flavour and funk. Cooking grilled cheese with mayonnaise might sound goyish, but believe me: It yields the most perfect golden-brown crust. And it isn’t greasy or easily burned, like butter.

Makes 1 sandwich

Two ½ in [12 mm] thick slices challah, homemade or store-bought

1 ½ Tbsp Pastrami Jam (recipe follows)
2 slices American cheese
1/3 cup [40 g] grated aged Gruyère cheese
2 tsp mayonnaise

Heat a seasoned cast-iron skillet (a nonstick pan will do in a pinch) over medium heat for 5 to 6 minutes, until hot. Lay out the bread on a cutting board or a plate. Spread the jam on one side of a slice of challah, and top with a slice of the American cheese. Add the grated Gruyère, and the second slice of the American cheese. Spread the outside of the second slice of challah with half the mayonnaise, shmearing it from edge to edge. Place on top of the American cheese, with the mayonnaise side facing up, to close the sandwich.

Lower the heat to medium-low. Carefully pick up the built sandwich and flip it, placing the mayonnaise-slathered slice face down in the center of the skillet. Cook the sandwich, undisturbed, for 4 to 6 minutes, until the cheese begins to melt. (Lower the heat if needed.) While the first side cooks, carefully spread the remaining mayonnaise on the top slice of bread. Carefully flip the sandwich, using a spatula. Cook for 4 to 5 minutes more, using the back of the spatula to lightly press down on the sandwich to encourage browning and melting.

Remove the grilled cheese from the pan and transfer to a cutting board. Cut into triangles and serve hot.


Pastrami Jam

1 Tbsp vegetable oil 
2 medium yellow onions, diced
8 oz [225 g] pastrami, chopped (Don’t trim the fat!)
½ cup [100 g] packed golden brown sugar
½ cup [120 ml] apple cider vinegar
¼ cup [80 ml] maple syrup

Heat a heavy-bottomed skillet over medium-high heat. Add the vegetable oil and heat until nearly smoking. Add the onions and cook for 5 to 6 minutes, until translucent, stirring often. Add the pastrami, stir, and cook for 3 to 4 minutes. Add the sugar, vinegar, and maple syrup and stir to combine. Bring to a simmer and cook until the liquid begins to thicken, 6 to 8 minutes, stirring as needed. Turn the heat to medium-low and cook for 1 hour more, stirring every 15 minutes to prevent sticking and burning. Remove from the heat. Using a food processor or an immersion blender, process the mixture to a jammy consistency. Transfer to an airtight container and let it cool. Store, covered, in the refrigerator for up to 1 week, or in the freezer for up to 3 months. Makes 2 cups [600g].

Recipe reprinted with permission from Chronicle Books.

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