In the booklet for the boxed set, "Highway", he states that the song "reminds me of the time I lived in Omaha as a kid and how we'd walk through cornfields and chew on pieces of grass. There were cold winters, and I had images of going to California. So I think in the song I'm talking to myself, frankly: 'How long you gonna stay here, Joe?' I really believe that 'Ventura Highway' has the most lasting power of all my songs. It's not just the words — the song and the track have a certain fresh, vibrant, optimistic quality that I can still respond to". The song has a "Go West, young man" motif in the structure of a conversation between an old man named Joe and a young and hopeful kid. Joe was modeled after a "grumpy" old man he had met while his dad was stationed in Biloxi, Mississippi at Keesler Air Force Base. He also stated "I remember vividly having this mental picture of the stretch of the coastline traveling with my family when I was younger. Ventura Highway itself, there is no such beast, what I was really trying to depict was the Pacific Coast Highway, Highway 1, which goes up to the town of Ventura."