The following Videos, "You Never Know," "Thought I'd Be Home by Now," "When Daddy Drank," and "You," are all Award winning videos for Jimmy.  

The last video is a video of a performance by Jimmy at the Arcada Theater in St. Charles, Ohio (a Chicago suburb) in August of 2019. He was on stage being accompanied by Nicholas Psyhogios, a friend and a fellow musician who is best known as "Chicago's Own Piano Man." Nick invited Jimmy to come be part of his show which was an opening act for the great Canadian artist, Burton Cummings, who sang with the famed group,  Guess Who. The show was sold out and Jimmy sang three songs with Nicholas accompanying him on piano.