I started playing along with Bob Dylan songs a few years ago, and at first sucked, but over time I got better and better, and a little while ago I started playing with bands sometimes at work (a bar). It’s a fun little instrument. One of the hard things that I had to learn was how to just freestyle, and improvise. But after playing with bands on songs that didn’t have harmonica parts already that I could just copy or songs that I didn’t know gave me a fast learning curve :P
Playing on covers of Sweet Home Alabama (Skynyrd) and Imagine (Lennon) is one of my favorite things I’ve ever done.