I don't know if you'd call him a "legend", but I was beaten in an amateur contest by country music artist Jim Ed Brown in 1952. He was about 18, and came on stage wearing a "Lash LaRue" suit (any one remember Lash LaRue?). Jim was known as J. E. back then. He had looks, talent, stage presence; and beat the bejabbers out of all of the competion - including my singing buddy and me.
Oh, I once carried Ramona Jones fiddle. She talked to me just like I was a real person. She's a very nice lady.
I was on a plane with the Steve Miller band; but I didn't know who Steve Miller was. My sons brought me up to date.