On a hard-backed chair in the upstairs study of his Toronto home, Gordon Lightfoot sat smoking and playing guitar.

On what he called his Quebec wicker table were his usual writing tools: a pencil, a pad of yellow lined paper, a cup of coffee and a bottle of whiskey. There was little else in the sparsely furnished room, aside from a telephone, a desk lamp and a large map of Canada on the wall. It wasn’t that Lightfoot lacked possessions or was short of money. His house was, in fact, a mansion. “Sundown” had made him rich. In June 1974, the sultry song and album of the same name had simultaneously topped the charts, bumping Paul McCartney out of the coveted number 1 position and taking Lightfoot to the biggest stages in North America. Things had kept rolling with “Cold on the Shoulder” and “Rainy Day People” hitting the Top 10. The momentum carried him across the Atlantic for his first European concerts, followed by a return engagement at London’s prestigious Royal Albert Hall. By late November 1975, after two triumphant final dates at New York’s Avery Fisher Hall, Lightfoot was back home. But there was no time to rest. With another album due, he had to come up with a new batch of songs.

Lightfoot was deep into his writing session when the phone rang. It was Bob Dylan. Lightfoot and Dylan went back a long way. They’d both come up during the folk boom, shared a manager in Albert Grossman, had hung out together and respected each other as song-writers. “What are you doing for the next two nights?” Dylan asked. He was in town with his Rolling Thunder Revue. Would Lightfoot like to join the two shows at Maple Leaf Gardens? Although his writing and recording usually took precedence, Lightfoot couldn’t resist.

Rolling Thunder was an entirely different way of touring. It began with the idea of Dylan, his buddy Bobby Neuwirth and mentor Ramblin’ Jack Elliott playing small venues while traveling around in a station wagon, then accumulated a larger, illustrious cast of characters that included Joan Baez, Roger McGuinn, Ronee Blakley, who’d just appeared in Robert Altman’s Nashville, and a stellar band featuring gypsy violinist Scarlet Rivera, future Americana star T Bone Burnett and ex–David Bowie sideman Mick Ronson.

Dylan’s tour had opened on October 30, 1975, in Plymouth, Massachusetts, and rolled through New England in two buses: one called Phydeaux, for the musicians, and the other nicknamed Ghetto, for friends. Dylan, his wife, Sara, and their kids traveled in a lime-green camper called Palm Beach. It was a wild, theatrical affair, with Dylan performing in white greasepaint, Allen Ginsberg along for the ride as resident poet and actor-playwright Sam Shepard documenting the antics, impressionistically, in a journal. Cameras shooting footage for a planned film called Renaldo and Clara captured the giddy spirit of the tour. It was as if a bunch of kids had run away and joined the circus. Spontaneity was the order of the day. During one stop, Dylan and Ginsberg visited Beat writer Jack Kerouac’s grave to sing a tribute to their On the Road hero. At another, John Prine and Bruce Springsteen showed up just to be in the audience.

Like a traveling Woodstock, Rolling Thunder was shaping up to be a major pop event. Who could resist a psychedelic musical caravan?

The tour’s destinations were being kept quiet, with handbills like advertisements for an old-timey roadshow getting distributed only at the last minute. But word quickly spread. Lightfoot knew all about it. Fans were thrilled to learn that Dylan had new songs and that he and Baez were performing together for the first time in a decade. Then there were all the famous musicians onstage at once. Additional guests were hopping on and off like passengers on a train. Joni Mitchell was supposed to appear only at Niagara Falls, but she enjoyed the tour’s communal feeling so much she stayed on for several dates. Now Dylan was inviting Lightfoot to take part in the crazy, star-packed shows scheduled for Toronto.

Dylan and his entourage dropped by Lightfoot’s house the night of November 30 to discuss it. Things got a little testy with Baez, Lightfoot recalls. “Bob and I had to negotiate with Joan right there on the second floor of my house, because she was worried about the running time. She kept saying, ‘There isn’t enough time, Bob. There isn’t enough time.’ Joan was kind of uptight but a great lady. In the end, Bob just said to me, ‘You’re booked anyway.’” Lightfoot was officially on board. As he casually told a newspaper reporter the next day, “They gave me a buzz when they got to town, to come down and do a few tunes, and that’s just what we’re gonna do.” Like it was no big deal.

Maple Leaf Gardens, home of Lightfoot’s favorite team, the Toronto Maple Leafs, was Canada’s most storied hockey shrine. But the arena also hosted plenty of concerts, including Dylan’s last Toronto appearance, when he shared the stage with the Band. The fifteen-thousand-seat venue quickly began filling up for the first Rolling Thunder show. Backstage was buzzing. The scene was a who’s who of rock nobility. Elton John was there. So too were David Clayton-Thomas, of Blood, Sweat & Tears fame, and Ronnie Hawkins, the man who’d groomed the Band for stardom.

Up to this point, the concerts had been running close to four hours. Dylan was in charge, orchestrating everything. He was clearly pleased to have Lightfoot along. On the first night, before singing a stark duet of “Dark as a Dungeon” with Baez, Dylan dedicated the traditional ballad to Lightfoot, who’d first sung it while still a member of the Two Tones. “We’re gonna do this one for Gordon tonight,” Dylan announced. “Gordon Lightfoot, is he still here?” Then, looking around, he whimsically added, “Thought I saw him walking toward the door—stop him!” During his next set, before a mesmerizing solo performance of “Love Minus Zero / No Limit,” Dylan called Lightfoot “one of my favorite songwriters in the world.”

Rolling Thunder’s cast shone brilliantly as well. Mitchell delivered a riveting version of her song “Coyote.” Elliott paid warm homage to Woody Guthrie with “Muleskinner Blues.” And Baez sang the haunting “Joe Hill” and two moving songs in tribute to the Band, “Long Black Veil” and “The Night They Drove Old Dixie Down.” Then she joined McGuinn for a soaring rendition of the Byrds’ epic “Eight Miles High.”

Dylan had given Lightfoot an important slot in the show, right before his own final set. It took a long time for Lightfoot to come out; he was backstage tuning guitars, his usual pre-concert ritual. Baez, acting as emcee, entertained the crowd with her impressions of comedian Lily Tomlin’s best-known characters. Then, when it finally came time, Baez introduced Lightfoot. As he walked onstage, Lightfoot looked every inch the handsome hometown hero, clad in denim with sleeves rolled up, ready to work, the spotlight illuminating his blond curls. He’d started out a decade earlier, playing a small room at Steele’s Tavern, a few blocks away on Yonge Street. Now he had the prime spot at the hottest concert of the decade.

Backed by his usual sidemen, bassist Rick Haynes, guitarist Terry Clements and pedal steel player Pee Wee Charles, Lightfoot launched right into a brand-new song: “Race Among the Ruins.” It was his latest poetic take on a tumultuous romantic life. “The road to love is littered by the bones of other ones,” he sang, “who by the magic of the moment were mysteriously undone.” The audience loved it. Lightfoot’s songs always took listeners on a journey, drawing them into stories rich in emotion and without a trace of artifice. Next up, he sang “The Watchman’s Gone,” one of his many songs steeped in railway imagery. By the time he closed with “Sundown,” his taut tale of sexual jealousy, Lightfoot had everyone cheering wildly. The following night, he added “Cherokee Bend,” about injustices suffered by First Nations people, and finished with “High and Dry,” an upbeat number he liked to call a “toe-tapper.” Meticulously crafted, the songs were nonetheless instantly accessible and sounded entirely natural. With the audience screaming for more, Neuwirth stepped to the mike and urged Lightfoot back. Once again, a simmering “Sundown” enthralled the crowd. Both shows ended with Lightfoot and Mitchell joining tour regulars, friends and family, including Dylan’s mother, Beatty, for a jubilant round of Guthrie’s “This Land Is Your Land.”

The December 1 show broke the four-hour mark. Everyone was ecstatic. Swept up in the euphoria, Lightfoot invited Dylan and the entire cast of more than seventy people back to his place for a party. The Rolling Thunder circus pulled onto Beaumont Road, a quiet cul-de-sac by a ravine in Rosedale. What took place in Lightfoot’s mansion was a rock-and-roll bacchanal. His blue-and-silver Seeburg jukebox was working overtime, pumping out a steady stream of Cream, Zeppelin, Doobies and Flying Burritos. Everyone was either drinking, snorting or inhaling something, and smoke floated freely about the sprawling house—past the grand piano, the slate billiard table and the Tiffany lamps all the way up to the master bedroom, with its Frank Lloyd Wright stained-glass window. The heavy consumption may explain why memories of the event are so fuzzy. Most people think there was one big noisy party; others believe there were two. Some recall one of Lightfoot’s friends, a six-foot-ten banjo player named Tiny, acting as security and greeting Mitchell, McGuinn, Rivera, Ronson and all the others as they arrived.

But almost everyone remembers Dylan’s buddy Neuwirth throwing his leather jacket into Lightfoot’s fireplace and filling the house with thick black clouds. Says Ramblin’ Jack, “Bobby was a very enthusiastic partier. I don’t remember all that transpired at Gord’s, because we drank to excess. But we were told we had quite a lot of fun.” Ronnie Hawkins, another Rolling Thunder addition, certainly recalls the fireplace incident. “Dylan was into drinking carrot juice at the time, and he and Neuwirth got into an argument. . . . Neuwirth just lost it and threw his jacket into the fire. It was like a smoke bomb going off.”

While revelry raged on the main floor, Lightfoot and Dylan were alone upstairs with their guitars, in a parlor room with a leaded bay window and floral wallpaper. Lightfoot had stripped down to a singlet, jeans and sandals. Dylan was still wearing his leather coat and fur hat. They seemed a mismatched couple, a study in contrasts. Here were two songwriters at the top of their games. But neither was comfortable in conversation, despite their friendship and mutual respect. Too guarded, or maybe too competitive. They did, though, share the common language of music. As others partied wildly below, Lightfoot and Dylan quietly traded songs. A recording made that night of Lightfoot playing Dylan’s “Ballad in Plain D” can be heard on the Renaldo and Clara soundtrack. A few photographs captured the historic exchange.

Each of them had started out the same way—alone in a room with a guitar, pencil and pad of paper. The discipline of that hard, solitary work created timeless songs that reached millions. Dylan had become the greatest songwriter of his era. Lightfoot was close behind. Although more workmanlike and straightforward, Lightfoot’s songs had an artful structure and poetic resonance that made them accessible in ways that Dylan’s weren’t. Both were highly prolific and idiosyncratic. After selling out the largest venue in the city, attracting a constellation of music’s brightest stars and hosting a fabulously decadent party, all these two artists wanted to do was retreat to a room and trade songs over acoustic guitars. For Lightfoot, as for Dylan, it was always about the song.