5. Dave Matthews Band
The Dave Matthews Band exist slightly outside the world of traditional jam bands. They had huge radio hits, a presence on MTV and, at least back in the 1990s, a huge audience of teenage girls. Many people come to their shows anxious to hear tunes like "Crash" and "The Space Between" and have little appetite for long moments of improv. But that is part of the DMB experience: The group works hard to make sure every show is unique and even the same songs are played differently from night to night. The amount of money they've made on the road over the past 20 years is just staggering, and it's easy to imagine that 20 years from now they'll still be at it.