I think the industry has changed, but good old fashioned legwork and salesmanship should work. I used to go around with a tape and songlist and business cards to clubs. I would try and call ahead to catch the owner. At some point you need to follow up and make sure the person who needed to hear the tape got it.
I am very shy and not much of a salesman, but I was surprised that it wasn't as hard as I originally thought to book gigs. Granted, our tape was pretty good, and our songlist contained a good mix of popular songs. I never enjoyed that aspect of being in a band, but it is neccesary to getting gigs.
It got alot harder when we tried to get gigs as an original band. It was hard to even get free gigs at amateur nights. The material was good. The recordings were even better than cover song demo tapes. But its a whole different deal than playing to the normal cover song crowd.
If you know people, it helps also. One of my former band members became a manager for a popular local cover band. He just kept on top of who needed bands and was very succesfull at keeping them booked. If you go to lots of clubs and get to know people, then that is often enough to get your foot in the door.
