Light a grill over high heat. Wash tomatoes and hot pepper. Pat dry, halve the tomatoes and drizzle both the tomatoes and hot pepper with a little olive oil; sprinkle with salt & pepper. When grill is hot, place the seasoned tomatoes, cut side down and the hot pepper on the grates. Grill for about 5 minutes per side or until tomatoes soften and have some grill marks. Turn the pepper several times but turn the tomatoes only once. Remove to a plate and set aside to cool.
Peel the tomatoes and discard the skin (or eat it). Halve the pepper lengthwise, remove the skin, ribs and seeds. Place the tomatoes and as much of the hot pepper desired in to a blender. Add the Worcestershire sauce and next 8 ingredients to the blender. Puree until mixture is smooth. Add the vodka or tequila and whirl until combined.
To dress the glass, use a slice of lemon to moisten the rim of the glass. Reserve slice for garnish. Dip glass into the steak seasoning to coat the rim. Add ice to the glass and pour in the cocktail mixture. Garnish as desired using things such as the classic celery, green olives, pepperoncini and just about anything pickled. Step it up a notch with things like grilled shrimp and meats like bacon, prosciutto, salami, etc. Top it all off with a generous grinding of black pepper. Sit back and enjoy!