Boxcar Willie - America’s Favorite "Hobo" Was Actually a Military Hero. You probably remember him as Boxcar Willie, the singing hobo with the rumpled hat, dirty face, and that pitch-perfect train whistle. But what if I told you the man who became the face of the Great Depression drifter actually spent 27 years in the cockpit of high-tech military aircraft? Did you know Boxcar Willie was a high-flying veteran, or did you always think he was a real-life hobo? Let me know in the comments! If you en