You can do a lot of the work in advance—marinating, stuffing, and rolling—and just put it in the oven about 45 minutes before you want to serve it.
How to Butterfly Steak
To prepare the flank steak so that you can roll it up, you’ll need to butterfly it (or have your butcher do it) so it opens up like a book. Butterflying flank steak takes a little bit of finesse, which is why we usually have our butcher do it for us. But it is doable. You’ll need a long, sharp knife and a steady hand. Orient the flank steak so that the short end faces you, place your hand down on the steak, and make a horizontal cut along the long side of the steak, cutting the meat almost in half, stopping when you still have about an inch to go. Then, open it like a book!
Flank Steak Marinade
After butterflying the steak, we marinate it for a couple hours in a simple olive oil and wine vinegar marinade. The marinade has:
Extra virgin olive oilRed wine vinegarGarlicFresh parsleyBlack pepper
Roll Up the Flank Steak With Filling
Once the steak has marinated, you layer the inside with prosciutto, fresh basil leaves, Parmesan cheese, strips of roasted bell peppers, and parsley. Then, you roll up the flank steak with the stuffing inside, like a jelly roll, and tie it up with string. You can do this several hours in advance before cooking. The rolled steak takes only about 30 minutes or so to cook in the oven. To serve, the steak is cut into rounds for a festive presentation. A version of this recipe has been floating around the Internet for years. We found it in a magazine maybe 15 or 20 years ago and photocopied a clipping. The likely source is a recipe for Italian Party Flank Steak that appeared in Parade Magazine in the 1990s. (Thank you to all of our commenters who also clipped the recipe and remembered the source!) Cover and refrigerate the assembled steak overnight. On the day you plan to serve it, remove from the fridge one to two hours before cooking, and let the steak come to room temperature before baking.
Customize the Filling
Use prepared pesto if you don’t have fresh basil leaves.Instead of Parmesan, use mozzarella, provolone, feta, or blue cheese.Add cooked mushroom slices or strips of raw pepper in place of the roasted red pepper.
Sides to Serve With Stuffed Flank Steak
Creamy Baked Mac and Cheese Roasted Parsnips Cider Vinaigrette Roasted Root Vegetables Cold Pea Salad Spring Vegetable Salad With Mint Pesto
Trader Joe’s sells a jar of roasted red peppers that works well as a substitute for roasting your own.
1/4 cup extra virgin olive oil 1/4 cup red wine vinegar 2 cloves garlic, finely chopped 2 tablespoons chopped fresh parsley 1/4 teaspoon coarsely ground black pepper
Flank steak:
1 flank steak (3/4-inch thick, about 1 1/4 pounds), butterflied 2 red bell peppers (see Recipe Note) Olive oil 6 to 8 thin slices prosciutto, or other cured ham 3 tablespoons chopped parsley 24 medium-sized fresh basil leaves 2 tablespoons grated Parmesan cheese Freshly ground black pepper to taste 1 bunch watercress, or baby arugula, for garnish
The butterfly hinge should be in the same direction as the grain of the meat. (Choose the longest straightest side of the steak as the hinge side, and the roundest most-curved side as the side to start the cut.) Open the flaps of the steak. You can even out the middle if you want so that the center is not as thick. (Note: There’s no need to refrigerate during cool weather. During hot weather, though, refrigerate for 1 hour. Then, let marinate at room temperature for the last hour.) Broil the halved red bell peppers until the peels are blackened. Remove from the oven, place in a bowl, and cover with a plate. After about 5 minutes, remove and discard the blackened peel. Remove the steak from the marinade, reserving the leftover marinade. Layer the steak with prosciutto slices, roasted red bell pepper, parsley, and basil leaves, leaving at least an inch bare at the ends. Sprinkle with Parmesan cheese and black pepper. Place in a shallow baking dish and spread any remaining marinade over the top. Serve, arranged on a platter, garnished with watercress or baby arugula.
