Start by taking the ribeye steaks out of the refrigerator. Pat them dry with paper towels to remove excess moisture, which helps achieve a better sear. Season both sides generously with kosher salt, cracked pepper, garlic powder, and paprika. Let them sit at room temperature for about 30 minutes.
In a cast iron skillet, heat 1 tablespoon of the oil over medium-high heat until it's shimmering but not smoking. This should take about 2-3 minutes.
Carefully place the seasoned steaks in the hot skillet. Sear without moving them for about 4-5 minutes, or until a beautiful crust forms. Flip the steaks using tongs and sear the other side for another 4-5 minutes for medium-rare, or longer for desired doneness.
Once the steaks are flipped, add the remaining oil, butter, rosemary, thyme, and halved garlic bulb to the skillet. As the butter melts, use a basting spoon to pour the melted butter over the steaks repeatedly for added flavor.
Insert a meat thermometer into the thickest part of the steak. For medium-rare, the internal temperature should be 130°F. Remove the steaks from the skillet and transfer them to a cutting board. Let them rest for at least 5-10 minutes.
While the steaks are resting, reduce the heat in the skillet to medium. Add the minced shallot and sauté for about 2 minutes until softened. Add the canned cherries (without the juices), chicken broth, honey, Dijon mustard, brown sugar, balsamic vinegar, and cornstarch. Stir to combine and let the sauce simmer for about 5-7 minutes, allowing it to thicken.
Slice the ribeye steaks against the grain and serve them drizzled with the cherry sauce. Garnish with additional fresh herbs if desired.