So this past year, the cover band I am in actual started to experience some local success. Nothing crazy, but we had consistent gigs at some casinos, restaurants, weddings, and a few corporate parties, and all made a few thousand bucks throughout 2013. Now that tax season is here, all those 1099s started showing up on our doorsteps. Fortunately I, unlike some of my other band members, saw this coming and kept a savings account that I added money to at the end of each month to the tune of what I expected to have to pay in taxes. Fast forward a bit, and I did my taxes and it turns out I was about right, so I'm in good shape. Some of my other band mates did not realize this however (and they didn't listen to me when I warned them), and are now freaking out because their tax returns have them owing some pretty large sums of money. For those of you out there who have been doing this longer than I have, any advice on the best way to handle this? Should we set up the band as a business? If so, what kind do you recommend? Would it be best for us all to just set up separate sole proprietorships? It seems to me there has got to be a better way of handling this, particularly since I know we can write off expenses (mileage, strings, etc) on our taxes if we have it set up properly, and end up owing uncle sam less. Any advice you can offer would be GREATLY appreciated.