Let's *pretend* you're in a band. Your band isn't trying to set the world afire with original material. You and your mates are just having a bit of fun, covering old favorites.
Songs In Your Fantasty Cover Band!
Now, you don't want to play a bunch of old Rolling Stones tunes, no matter how much fun they are to play, nor how much the bar's proprietor wishes you guys to do so. Instead of Satisfaction, you pick Dead Flowers instead. Now, every one's happy, eh? OK, on the other hand, you can't just fill your set list with a bunch of obscure indie tunes, either. No one is going to appreciate tunes from Yourcodenameismilo or Amusement Parks on Fire etc. So the trick, really, is to pick an eclectic set of songs which challenges you and the audience; songs which don't alienate the audience or bore the heck outta the band.
Out There - Dinosaur jr
Killing Moon - EATB
Dead Flowers - Rolling Stones
It's No Game - Bowie
Sweet Jane - Lou Reed
Godless - Dandy Warhols
Coffe & TV - Blur
Up The Bracket - Libertines
Monkey Gone To Heaven - Pixies
Kings & Queens - Aerosmith
And if me and me mates haven't been booed off the stage we play a bunch more Bowie tunes...cause that's really all we know. :-)
PS Being a hack musician isn't a requirement to join this thread...but is sure helps. ;-)