From a memorable performance with Arcade Fire to a collaboration with the dance troupe La La La Human Steps, David Bowie put his stamp on Montreal's artistic map.

Here are few memorable moments involving Montreal and Quebec in a career that spanned five decades.

Arcade Fire's 'Wake Up'

David Bowie has a strong connection with Montreal's most popular indie rock export, Arcade Fire. Bowie took part in several memorable performances of the band's hit song, "Wake Up."

He also appeared as a backup singer on the 2013 hit song "Reflektor."

On Monday, Arcade Fire's frontman, Win Butler, mourned his passing.

La La La Human Steps joins him on tour

Always looking for new ways to incorporate a range of performance styles into his stage shows, Bowie collaborated with Montreal dance troupe La La La Human Steps for the Sound + Vision tour in 1990.

Édouard Lock, the group's founder, said Bowie made decisions based on the "adventures he wanted to live."

"He never made decisions based on what would have been acceptable," Lock told CBC.

"He made society run after himself rather than him trying to see how to best fit into the mores of the time."

Louise Lecavalier, an icon of Canadian dance, joined him on the tour, which opened at Quebec City's Colisée on March 4 of that year.

Bowie records an album in Morin Heights

Bowie was among the artists who laid down tracks at Le Studio, a cabin in the woods in Morin Heights, Que. — hailed at the time as being one of the best studios in the world.

André Perry, owner of Le Studio, met Bowie when he went to Morin Heights to record his 1984 album, Tonight.

David Bowie Le studio

David Bowie recorded his 1984 album Tonight at Le Studio. (André Perry Studios)

"At the time that he came to do this album, it was a difficult part of his life.... He was always experimenting ... and I believe that in a way, his career was a mix of being a very highly creative person and a person who had to deliver to the pop world," Perry said.

"This is a difficult place to be — having to deliver hits and at the same time being highly creative and do things that are not necessarily aimed at a very large market."

Diamond Dogs tour debuts at the Forum in '74

Bowie launched his extravagant Diamond Dogs tour at the Montreal Forum in 1974. The six-month North American tour marked the end of his Ziggy Stardust character and a move away from "glam."

In 1983, Bowie kicked off his North American Serious Moonlight tour in Quebec City. He also started his A Reality tour in Montreal in 2003.

Sold-out shows in '91

In December 1991, David Bowie and his band Tin Machine performed at La Brique, a Montreal rock bar. They played to a sold-out crowd on both nights. 

David Bowie performs with Tin Machine in Montreal0:46

"The kind of material that we have isn't the kind of material that everyone feels comfortable with. We're not a comfortable band," said Bowie.

Montrealers reminisce

Montreal music fans, including Montreal Gazette political cartoonist Terry Mosher, took to social media to share their own memories of Bowie. Here are a few of them: