Preheat an oven to 375 F.
Roast the tomatoes. Toss the tomatoes with olive oil, sliced garlic, fresh basil, salt and pepper in a small baking dish. Roast for 40-45 minutes, until the tomatoes are soft and jammy.
Toast the orzo. Heat the remaining olive oil in a large skillet or braiser over medium heat. Add the minced shallot and cook until translucent. Add the orzo to the pan and cook, stirring often, for 2-3 minutes until the orzo is coated in the oil and lightly golden brown.
Cook the tomato paste. Add the tomato paste to the pan and toss to coat the orzo in it. Cook, stirring constantly, until the tomato paste has darkened in color--about 2 minutes. Add the broth to the skillet, season with salt and pepper and bring to a simmer. Add the tomatoes, garlic, and basil from the dish of roasted tomatoes and stir well. (Save the roasting liquid for a vinaigrette or for drizzling over the finished orzo!)
Simmer. Cover the skillet reduce the heat to low and cook for 12 minutes, stirring every couple of minutes to prevent sticking. Uncover the orzo and stir in the butter and heavy cream. Continue to simmer until the orzo is cooked through.
Finish. Remove from the heat and stir in the parmesan cheese and more minced basil. Season to taste with salt and pepper and serve the roasted tomato orzo warm.