Favorite laid-back drinking/dining spots (ideally with live music)?

What are y’all’s favorite spots to have a few drinks, listen to some music, and have some decent food while catching up with friends? I’ve heard good things about the Flat but haven’t gotten the chance to go there yet. I love the idea of listening to local DJs in a casual setting so it’s on my must-visit list.

Also interested in hearing about y’all’s favorite beer gardens, casual bars, and other spots that are fun but not too try-hard like some of the places on Washington or Midtown.