Yes, the Ugly Duck used to be a strip club. I heard (probably 10 years ago) that they had decent food, but I've never eaten there. My go-to for the "bar" scene is Leroy's. (Can't believe I forgot about them!) They have my favorite wings in Wooster (better than Muddy's), and they have little pizzas that are perfect for one person. A family tradition of ours is the day we decorate our Christmas tree, we get pizza and wings for dinner and watch Home Alone. We used to get our pizza and wings from one of the main chains (Donato's, Papa John's), but once we started getting them from Leroy's, we're never going back.
The Olde Jaol (tavern) used to be a good option for our family, but over the years it's kind of turned into Jerry's 2.0... the food is good, but it either takes forever to get a seat, or the service is slow. More than once my wife and I have sat down, never got waited on, and left. And with their a la carte menu, it gets surprisingly expensive real fast.
This might be a hot take, but if we want your typical chain "Applebess" type food, we go to Beef O' Brady's. They're newer to Wooster, a block down from City Square. But they have really good daily specials, the prices are great, and we've enjoyed the food. And they have ALL the flavored lemonades, which my daughter and I love!
Oh, how could I forget?!? If you're on a budget and have an AARP card, go to Green Leaf (closer to the north end of Wooster). Okay, you're allowed to go there without the card, but everyone will stare at you. But the prices are great, and the food is basic but good.