Gamblers, racketeers and the world’s greatest entertainers – especially American jazz musicians – flocked to Montréal, notably between the two world wars when Montréal’s Little Burgundy neighbourhood was dubbed the “Harlem of the North.”

Montréal quickly became the nightclub capital of Canada, and her fabled Sin-City era would continue well into the 1950s.

Today, Montréal remains a hotbed of jazz. The city is home to the world’s largest jazz festival as well as live music in the city’s swinging jazz clubs seven nights a week. While Montréal’s Sin City heyday is behind her, Montrealers still love letting the good times roll long after most other cities have rolled up their sidewalks and gone to bed.

Sin City Montréal

Jazz, a style of American music birthed in New Orleans around the turn of the 20th century, migrated north to Montréal, hometown of global jazz icon Oscar Peterson, Maynard Ferguson and Oliver Jones.

Montréal became home to countless jazz nightclubs such as the famous Rockhead’s Paradise, a three-storey show bar located on the corner of de la Montagne and Saint-Antoine Streets. Founded by Rufus Rockhead in 1928, Rockhead’s Paradise was where Louis Armstrong went after performing at the Montréal Forum or uptown clubs, and it was where Ella Fitzgerald made her Montréal début in 1943.

Just around the corner from Rockhead’s on de la Montagne Street was another popular Black club, the Café St-Michel, home of Louis Metcalf’s International Band. Metcalf had been a trumpeter with Duke Ellington and Jelly Roll Morton before bringing bebop to Montréal.

Pianist Oliver Jones, a former protégé of his idol Oscar Peterson, was just 10 years old when he first performed at the Café St-Michel in 1944.

Mr. Jones once told me, “It was across the street from Rockhead’s Paradise, which was the first Black-owned club in all of Canada. The St-Michel was a little rougher. Rufus Rockhead never let anything get out of hand although there was always pressure from authorities to close him down. But I remember playing in the St-Michel and saw a lot of what I wasn’t supposed to see – girly girls and strippers. But the people there, there was always someone looking out for me.”

During Montréal’s 1920s to 1950s golden age of jazz, everybody from Dizzy Gillespie to Duke Ellington made their way to the city. Even Frank Sinatra headlined Chez Paree on Stanley Street during a residency there in 1953.

Let the Good Times Roll

Jazz declined in popularity in the 1960s thanks to the rise of rock’n’roll but bounced back in Montréal when legendary impresario Rouè-Doudou Boicel founded the Rising Sun Celebrity Jazz Club in 1975. The club was located on Sainte-Catherine Street, opposite where the Festival International de Jazz de Montréal’s Maison du Festival is located today, in the Quartier des spectacles.

“My deepest friends who helped me were Taj Mahal, Buddy Guy, Art Blakey, John Lee Hooker and Dizzy Gillespie, who came to Montréal whenever I needed money,” Boicel told me. “That was a guarantee my place was packed.”

Boicel also founded the short-lived Rising Sun Festijazz at Place des Arts in 1978 – presenting everybody from Sarah Vaughan to Dexter Gordon – before the Festival International de Jazz de Montréal was established in 1980.

The Rising Sun is gone now, as are Montreal’s famed Sin City-era jazz clubs like the Café St-Michel. Rockhead’s Paradise closed in 1980. But a vibrant local jazz scene has grown alongside the Festival International de Jazz de Montréal, which is very supportive of local musicians.

Festival International de Jazz de Montréal

The arrival of the Festival International de Jazz de Montréal in 1980 signaled a new era of Montréal jazz. Many jazz clubs have opened since and are especially busy during the festival.

Each year the ten-day jazz festival books some of the biggest acts in the music business, showcasing some 3,000 musicians from 30 countries headlining 500 indoor and outdoor concerts – ticketed and free – on 20 stages.

The Festival International de Jazz de Montréal is the world’s largest according to Guinness World Records, and each year begins during the last week of June.

Upstairs Jazz Bar & Grill

Close to the major hotels downtown and popular with tourists, the intimate Upstairs Jazz Bar & Grill books local musicians such as renowned drummer Jim Doxas, blues queen Dawn Tyler Watson and soul legend Michelle Sweeney.

Jazz royalty performing at Upstairs over the years includes international headliners Sheila Jordan, Jimmy Heath, Joe Lovano, former Oscar Peterson drummer Alvin Queen, Jeff Healey and jazz legend Ranee Lee, who recorded her Juno Award-winning live album at Upstairs.

Upstairs was the first off-site jazz club to be part of the Festival International de Jazz de Montréal, hosts regular jam nights for jazz musicians attending McGill and Concordia universities, and is ranked by Downbeat Magazine as one of the top jazz clubs in the world.

Dièse Onze Jazz & Restaurant

Dièse Onze, in the hip Plateau district, is very intimate, looks and feels exactly like a classic jazz club should, and features live music every night by such musical guests as Juno Award-winning soul diva Kim Richardson and the popular groove and improvisation-fueled collective The Brooks. In February 2018, DownBeat Magazine named Dièse Onze as one of the top jazz clubs in the world.

More Montréal jazz clubs

The underground artist-run Résonance!, in the Mile End district, books jazz, classical and experimental musicians year-round, including the popular Kalmunity Jazz Project on Sundays.

Modavie, in Old Montréal, is a French bistro that features live jazz and blues seven evenings a week, showcasing local performers. The old-school jazz feel is accentuated by the bistro’s stone and wood décor.

Montréal Jazz History Walking Tour

During the jazz fest each year, professional tour guide Leah Blythe presents her popular Montréal Jazz History Walking Tour. The two-hour tour through downtown Montréal tells the story of jazz and its connection to the city from the 1920s until the foundation of the Festival International de Jazz de Montréal in 1980. You’ll see what has become of such former clubs as Rockhead’s Paradise, the Rising Sun and Chez Paree. For more information about the walking tour during the jazz festival and year-round, email Blythe at leah.m.blythe@gmail.com.