It is not at all clear that the "business" is obligated to pay you, although the fact that you say Walter claimed to have sent you a check strongly supports that interpretation. What was Randy's role in this situation? Is he your agent? Walter's agent? An employee of Walter's business? How did he get the authority to hire you? On whose behalf was he acting when he hired you? Why are you dealing with Randy if it is Walter who owes you money? If Walter wrote a check to you personally, then he can stop payment on his check if it is "lost in the mail" and write a new one, or present you with a copy of his cancelled check to prove it was cashed.
I see no reason to believe that either you or the defendant in your small claims case will be required to hire an attorney. It is unlikely that you would have agreed to work for nothing, but establishing the exact amount that you were promised in court will require you to present witness testimony (in the absence of a written contract) to establish the amount. Will Randy so testify? Will Walter? Will your colleague? If Walter does not show in court you win--then you still have to collect.
It only takes thirty seconds to write a binding contract. I,xxxx agree to perform at yyyy location on zzzz date for aaaa dollars to be paid by cccc at the time of or the performance or within ddd days following the performance. Both parties sign. Do it on a napkin--it is still better than a lying contest in court. Or insist on a check before you start to play. If the payer says he has to wait to be paid by the wedding planner, agree to hold his check until xxx days later. Wait as agreed then deposit his check. His bounced check is all the proof you need that you were not timely paid.
Nothing you say or hear on the telephone with anyone is proof in court. Unless the people you talk to will show up in court on the day of your trial and tell the same story, you have nothing except information. Use the mail-registered return receipt requested.
Join the f////king musicians union.