Do you love attending live concerts? If you do then this would probably interest you. Artists and musicians who are not that famous occasionally perform free in order to get the general public to know about them and their music. Such concerts are normally either free or they'll be low-priced. I've attended such a concert myself and I wouldn't say I was disappointed. Give it a try some time and save some moolah in the process.
I live in a city where there is constantly something happening for free in the streets and parks. I can't complain about suffering from a lack of entertainment. Also, there are a few sites on the internet that offer free passes to exhibitions. I just recently went to a stunning photo exhibition, admiring the work of Henri Cartier Bresson for free.
There are a lot of underrated bands no matter where you are, from street performers to free music festivals, music is everywhere so you should never have to look too hard. If you don't mind paying a small fee there are even music events that feature dozens of well-known bands/artists as well as dozens of new and upcoming artists that are worth seeing, a good example of such a festival (and my personal favorite) would be Warped Tour, more of punk/hardcore style of music but for less than $100 you can see something upwards of 30 bands in one day and even get to meet and socialize with them.