Wailin’ at the Windsor

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This article was published 17/09/2023 (1096 days ago), so information in it may no longer be current.

The Windsor Hotel was like the Tramp, the famous movie character portrayed by its most famous guest.

It may have been a little worse for wear sometimes, but it was beloved by many.

Charlie Chaplin’s stay at the 120-year-old Garry Street inn, which burned down Sept. 13, spreading smoke throughout Winnipeg’s downtown, is just one of many reminiscences that have wafted through the minds of city musicians, artists and spectators alike.

“I’m sad to see it go, because every time I drove past it I’d have a memory,” says Big Dave McLean, the blues singer and guitarist who played at the Windsor countless times and hosted his blues jam there for 28 years.

The hotel was mostly known as a music venue in the past 40 years, especially as a blues joint during the 1980s,’90s and 2000s when it was managed by Rick Penner. In recent years it sat vacant. It had been officially shuttered by a March public health order.

The Windsor brought in metal and punk bands in the 2010s until 2019, including the British proto-metal group Hawkwind, KEN Mode, the Juno Award winners from Winnipeg, and the fiery hardcore band SNFU.

McLean’s weekly jam welcomed musicians showcasing their guitar licks, or gave audiences a rare glimpse of award-winning stars who’d drop in after a gig at a bigger stage earlier in the evening.

“I jammed there with Colin James and Jeff Healey one time,” McLean says of the two Canadian blues-rock greats. “I’ve known Colin for years and years; they had a show at the convention centre and they knew I was playing at the Windsor. They came over after and I got them on the stage and they fired it up.”

He also remembers being in the crowd watching British bluesman Long John Baldry, as well as countless Canadian blues acts, including the Downchild Blues Band, Jack Semple, Sue Foley and Dutch Mason.

“There’s memories I have of the Windsor when I wasn’t playing at all, I was watching other people play,” McLean says. “We had big-name American acts but we had our own big-name Canadian acts coming through and it was wonderful.

“There were a lot of good local blues acts, too — Brent Parkin, Billy Joe Green… the list goes on and on.”

Green, who calls the Windsor’s demise “a sad state of affairs,” remembers a raucous crowd in 2004 for two gigs that became part of his album Muskrat Blues and Rock & Roll.

Another time, one of his audience members was just as enthusiastic and even more famous — former federal NDP leader Jack Layton.

“He was there and he came right up and he requested All Along the Watchtower,” Green says of the Bob Dylan song popularized by Jimi Hendrix and which Green plays regularly live. “He hung out there and he loved the band. We did it and we were happy to do that.”

The Anishinaabe guitarist said the Windsor’s welcoming atmosphere made it one of his favourite places to play and watch bands.

“It was loud and crazy. They were enthusiastic and they lined up around the block to get in that place,” Green remembers of the venue’s heyday. “People felt comfortable there and you felt safe in there.”

The Windsor was a regular stop on Canada’s blues circuit for top Canadian acts, as well as artists from the blues mecca of Chicago, who would often perform there as part of the Winnipeg International Jazz Festival.

Among them was Hubert Sumlin, the longtime guitarist for blues legend Howlin’ Wolf, who played the Windsor during the 2004 jazz fest.

Sumlin’s guitar licks on songs such as Killing Floor and Smokestack Lightning inspired the Stones, Led Zeppelin as well as other British Invasion acts of the 1960s.

“I played there with the Perpetrators when we backed up Hubert Sumlin; that was amazing,” McLean says of the gig, audio recordings of which have been posted on YouTube to mark the historic occasion.

Sam Smith, who booked bands at the Windsor from 2013 to 2017, brought in metal groups from afar, such as Hawkwind, to reverent audiences, as well as Winnipeg bands on the rise, such as hardcore punk group Comeback Kid, to exuberant crowd-surfers.

He said it was sad to see the hotel burn down, but he holds few sentimental thoughts about the place. Booking bands to play what had become a decaying dive bar was difficult.

“It was a challenge to get a band to play there,” he says. “There was no green room for them to relax and all the (hotel) rooms were full.”

Jesse Matthewson of KEN Mode remembers rocking the Windsor too, after metal and punk found a home there in the 2010s. The odd way the stage was set up had its pros and cons.

“I distinctly remember playing there with Full of Hell in 2013, with Dead Ranch in 2014, and Conduct in 2015. All super solid shows,” Matthewson says. “That weird wood thing at the front of the stage was kind of frustrating as a performer, though it did kind of keep patrons from spilling beer on your pedal board.”

While the Windsor made its recent history as a music venue, it was Chaplin, the silent-movie superstar. who gave the hotel its biggest brush with greatness more than a century ago.

He stayed at the inn in 1914 when it was called the Le Claire Hotel. He had been performing on the vaudeville circuit at the Walker Theatre — known a century later as the Burton Cummings Theatre — when he wrote a letter to his brother on hotel stationery saying he was done with vaudeville and was going to Hollywood to try his luck in the movies.

One year later, Chaplin starred in The Tramp, and his portrayal of the title character would become one of the most famous figures in the history of cinema, one he portrayed on several occasions.

The Tramp, and Chaplin, lived on in a 2001 mural on the northern wall of the Windsor, painted by Winnipeg artists Mandy van Leeuwen and Jen Mosienko, adapted from a scene from Chaplin’s 1918 film, A Dog’s Life.

The painting, which Penner commissioned along with Take Pride Winnipeg, shows movie curtains pulled aside, revealing Chaplin as the Tramp, holding a white dog with several people surrounding him. A caption told the Chaplin-Windsor story.

Van Leeuwen and Mosienko also painted portraits of blues legends B.B. King and Robert Johnson on the front of the hotel, as well as a likeness of the Tramp peering out at Garry Street from a second-floor balcony.

“The history of that place, it’s a backbone of Winnipeg’s culture and music scene,” van Leeuwen says.

She has worked on 44 murals in the city, according to the Murals of Winnipeg website, but a muralist has no control over the future of their work once the paint dries.

The Chaplin mural at the Windsor Hotel wasn’t the first of her works that’s been destroyed by fire, demolished or painted over. Several are remembered in the website’s “Rest in Peace” section.

One she painted with Franklin Fernando at 847 Notre Dame Ave., to mark Folklorama’s 50th anniversary in 2019, remains intact but can’t be seen as it was intended. A new building was erected right next to it a year later, leaving little room to view the 1,136-square-foot work.

“It’s sad that a mural goes away but there’s not much you can do,” she says. “(The Chaplin) mural has had a long life of being able to be there in front of everyone compared to something like that, so I guess I can be grateful it got to be that way.”

Alan.Small@winnipegfreepress.com

Twitter: @AlanDSmall