When Tom Cochrane went supernova with his 1991 harmonica-honkin’ hit “Life Is a Highway,” he was singing from experience. At the time, the Canadian rocker—born in 1953 in Manitoba and raised in Toronto—was nearly two decades into a musical journey marked by many twists and turns. In the mid-’70s, Cochrane debuted on the Toronto scene as a folky singer/songwriter before joining Red Rider, whose polished fusion of Floydian prog, New Wave modernism, and fist-pumping arena-rock made them Canadian-radio fixtures in the early ‘80s. But with Cochrane’s raspy yet radiant voice and inspirational lyrics becoming more central to their identity, the group rebranded themselves Tom Cochrane & Red Rider and shifted course into the heartland; earthy anthems like “Big League” and “Boy Inside the Man” paved the way for his solo coup with “Life Is a Highway.” That song would drive sales of Cochrane’s 1991 album, Mad Mad World, past six million copies en route to four Juno Awards (and, the following decade, the hit entered the kid-pop canon via Rascal Flatts’ countrified cover for the Cars soundtrack). In the 21st century, Cochrane has averaged just one new album per decade, but then he’s more than earned the right to travel life’s highway at his own leisurely pace.