"Little Man" tells the story of small businesses that couldn't keep up with larger corporations, often referred to as "the little man." The lyrics paint a picture of nostalgia and loss, as the narrator revisits towns and sees storefronts that are now empty and boarded up, like they never existed. This song, from his album High Mileage, captures the feeling of watching familiar places disappear, reflecting on the changes time brings to local communities. It plays like a heartfelt tribute to the fading memories of a simpler past.