“Jack and Diane” (John Cougar Mellencamp) – This little ditty is guaranteed to remind you why you are on a road trip to begin with: because you are experiencing life. It's a song reeking of nostalgia, and when the line “hold onto sixteen as long as you can” blares through the speakers, you are sure to remember when you uttered those very words and swore that you’d do just that — hang onto sixteen forever; it was a feat that then seemed so easy. “Jack and Diane” reminds the travelers that there is something bittersweet in not being sixteen anymore and something bittersweet in how fast time flies; it tells the traveler that growing old sucks, but still it’s better than the alternative.
“I Wanna Be Sedated” (The Ramones) – Fast paced and packed with anticipation, “I Wanna be Sedated” attests to the ingrained excitement a road tripper feels when just starting out. There’s gas in the tank, a mug of hot coffee in the cup holder, and the sun is rising over the mountains. With the wind in your hair and the Ramones on the radio, you put the petal to the metal and excitement rises to the point where you might really need a sedative. “I Wanna Be Sedated”, however, is a song that must be listened to in small doses. Hearing the same phrase over and over again eventually gets unbearably annoying, leading you not to mind as much if you accidentally drive off a cliff.
“What a Wonderful World” (Louis Armstrong) - There is no better song to play while driving through the most beautiful parts of the world than one that talks of the earth’s brilliance. Whether you’re driving down an ocean-side highway letting the smell of salt water tickle your nose hairs and hearing the slap of water as the tide hold hands with the beach, or driving down a curvy mountain road at sunset and glimpsing those few moments when an untouched forest forms a purple hue, “What a Wonderful World” is sure to give you insight into what that very song was about in the first place.
“On the Road Again” (Willie Nelson) – The reason for this song’s presence on this list is completely self-explanatory. If you don’t know why to include this song when taking even the shortest road trip, then you probably should just travel by trains, planes, but never automobiles.