Although his career eventually meandered into the realm of stand-up comedy and acting, beloved Scotsman Billy Connolly set off as a musician. His first earnest steps in the industry came in 1965 when he co-founded the folk-rock band The Humblebums alongside guitarist Tam Harvey and singer-songwriter Gerry Rafferty.
Following his stint with Connolly in The Humblebums, Gerry Rafferty soared to global recognition alongside his former school friend Joe Egan in Stealers Wheel. Between 1972 and ’75, the band released three albums, but their US number one of ’72, ‘Stuck in the Middle with You’, reaped the highest praise, famously serving as a fine dance tune for Michael Madsen in Reservoir Dogs in 1992.
By the mid-1970s, Stealers Wheel had dissipated amid financial woes, and Rafferty sought new management and funding for his first solo endeavour, City to City. Fortunately, Jon Brewer, an aspiring publisher and manager who had previously worked with David Bowie and Alvin Lee, among others, was a big fan of Stealers Wheel and agreed to meet Rafferty in London.
“His wife had just given birth to their daughter, and he told me that he didn’t have any money to buy nappies,” Brewer recalled in a 2019 conversation with Louder Sound. “He said, ‘I’ll play you something’. And he played ‘City To City’ and ‘Baker Street’ – a demo without the sax part. And I went, ‘I’ll fund the album. And here’s five grand, in cash, to help you.’”
City to City, released in 1978, became a huge career success for Rafferty, thanks to its wealth of charting singles, most notably, ‘Baker Street’ and ‘Right Down the Line’. The album provided the singer-songwriter with financial solvency and a segue into a comfortable solo career. “And that’s when the fun started,” Brewer commented on the momentous release.
Through the ups and downs of his career, Rafferty remained close with Connolly, who concurrently blazed a trail on screen and on stage as a comedian. Reflecting on the pair’s friendship during his interview with Louder Sound, Brewer remembered the wicked sense of humour they shared.
“He had this great friendship with Billy Connolly, and Billy told me this amazing story,” Brewer said. “Gerry was a joker – he used to joke all the time, an absolute nutter. Him and Billy used to play a game. Do you remember how old ladies used to have those little baskets on wheels they used to push around the shops? Well, in Glasgow, it was always raining, and they’d go down Sauchiehall Street on a Saturday and play this game”.
He added: “Gerry had a glass eye – I didn’t know this until Billy told me this story – and they’d wait until it was really pouring, and they’d go out, and all the old girls would put up their umbrellas. And Gerry would barge into their umbrella, shout ‘Oh my god!’, and as he hit the ground, he’d take his glass eye out and let it roll on the pavement.
“Some of these old ladies used to pass out. Billy said, ‘We got 10 points if they passed out, 5 points if they screamed…’ He was a wonderful character in those days.”
Rafferty sadly passed away in 2011, aged just 63, from multiple organ failure. He had suffered a lifelong addiction to alcohol which intensified following the death of his older brother Joseph in 1995.
In the 2012 BBC Two documentary Right Down The Line, Connolly reflected on his and Rafferty’s troubled relationship with alcohol. While the former managed to quit in 1985, Rafferty felt comfortable in his habit.
“I thought, ‘Oh, God almighty,’” Connolly said of Rafferty’s worsening addiction. “I’d read somewhere with alcoholics, you should tell them once, not twice or ask them, so I said, ‘Listen, are you OK with this drinking? Do you feel comfortable with your drinking?’ And he said, ‘Yeah, it’s not a problem’, and I said, ‘OK.’”
Elsewhere in the documentary, Connolly revealed that he remained close with his Humblebugs bandmate to the very end. “I was texting memories and things, and he was laughing, and we laughed right up to the very end. He knew it was time to go. And he went,” Connolly remembered before his smile faded and tears came to his eyes.