Listen to this track by beloved Canadian singer-songwriter and Orillia Ontario favourite son, Gordon Lightfoot. It’s “Carefree Highway”, an international hit as taken from his 1974 album Sundown. This song was one of several in his catalogue that scored a top ten placement on the US Billboard Hot 100. Otherwise, this song made the easy listening charts and the country charts in his home country of Canada, where he’d become rightly held as a national treasure.

Like Bob Dylan, Lightfoot was managed by Albert Grossman during the 1960s, and was on many of the same scenes. During that time his material was covered by many, including Elvis Presley, Marty Robbins, Judy Collins, and Peter, Paul, and Mary, among others. By the early 1970s and after defecting from United Artists to Warner Brothers, Gordon Lightfoot settled into a sound of his own that mixed acoustic folk-rock with a smooth country feel, along with a dash of sorrowful strings for good measure that gave his output a heavy shot of melancholy. The period between 1970 and 1978 is looked upon by many as his golden period that had him enjoying massive exposure on Canadian radio across the dial. For all of his ubiquity, it was easy to take him for granted.

On “Carefree Highway”, it was also easy to miss what lay beneath his gentle, made for radio play, and easy on the ears sound, to wit; an ocean of bittersweetness, much of that fueled by what seemed to be personal regret, not to mention the songwriting savvy it took to deliver it so poignantly to listeners. 

The song’s title was inspired by a stretch of highway in Arizona actually called “Carefree Highway” by locals where Lightfoot traveled while on tour there. The song isn’t so much about that specific trip or about that place as much it is about the idea of being out on the road alone in retreat in order to stave off unhappy recollections. This song is less about having no cares than it is about a sense of utter disconnection. It’s a tale that reveals the lasting heartbreak over an old flame who is forever out of reach, still haunting the narrator’s memory. It also reveals the depths of Lightfoot’s talent at being able to fashion a compelling and effervescent melody that sounds so contented to lyrics that directly contrast it. As a result, rather than the song being one-dimensional and piteous, it’s poignant, wistful, and bittersweet instead.

And what about the story found in this tune? Apparently it’s biographical, with an actual woman named Ann whom Lightfoot saw when he was in his early twenties. It was one of those cases in one’s life where love blossoms, but a shared path into the future doesn’t follow. It’s a story of could-have-beens and the loss of potential happiness that lingers for years afterwards. Lightfoot tells the story:

“There was a real Ann. It reaches way back to a time when I was about 20 or so. It’s one of those situations where you meet that one woman who knocks you out and then leaves you standing there and says she’s on her way. I heard from her after a Massey Hall concert many years later; she stopped by to say hello. I don’t think she knew that she is the one the song was about, and I wasn’t about to tell her.” (Read more Lightfoot song background info here)

It doesn’t get more real than that; a bond of love, a wound that never quite healed, and a silent burden when the person in question walks into one’s life again, unaware of the inner turmoil they cause. That is the other side of the coin when it comes to loving someone, isn’t it? You get the connection and the companionship that gives you that sense of home that we all look for in a loving relationship. But when you part ways you never really stop loving them even if the way you love them changes in your heart after its all over. That dull, melancholic ache will always be with you no matter how many highways you travel afterwards without them. It lives side by side with the memories you most cherish that include them. That’s the deal when it comes to love. That’s a big part of the risk, too.

Gordon Lightfoot is an active singer-songwriter today, despite past health issues and premature rumours of his death. A two years ago, Lightfoot embarked on what was called “50 Years On The Carefree Highway Tour”, a title that his agent came up with perhaps without the knowledge of that to which the carefree highway actually refers. Take a read of this interview that was conducted around that time that talks about his career that now spans half a century.

Enjoy!