Peppermill is a Vegas must see. I've only been there once years back, but it's definitely one to visit. As was stated above, the Bootlegger is old school Italian with a decent menu and prices. I used to stop in for happy hour when I stayed at Silverton a lot. Very comfortable and don't worry about bring your chrome or glass cleaner as you won't need it. I've never been there for late night entertainment, but will try one of these days. From what i've read, it's not uncommon to have big name stars stopping by to sit in for a song or two.
Good Luck!
Ric at Joes