With all the times I've been to CityWalk, I've never been to Rising Star. It sounds like I'm missing out on something. Definitely gotta check it out next visit.
My favorite places to hang out in the evening are Pat O'Brien's or Margaritaville. Both are fun, lively, and usually have good live music playing. The best place to get the most drink for your money is Fat Tuesday's. Decently priced, delicious, and fairly strong.
Being a big sports guy, my favorite place during the day, or night, is NASCAR Grille. A lot of TVs, decent food, and they usually have beer/drink specials.