Not a bad list but where is Steppenwolf and Weeknd? Drake should be much higher on this list. He will easily go down as the most popular and talented artist in Canadian history despite what the critics (tradiitonal people) here might say. He is one of the only Canadian artists who has literally changed the landscape and direction of pop music and hiphop music. No other artist on this list did that on a grand scale
The sixth generation of country music continued to be influenced by other genres such as pop, rock, and R&B. Richard Marx crossed over with his Days in Avalon album, which features five country songs and several singers and musicians. Alison Krauss sang background vocals to Marx's single "Straight from My Heart." Also, Bon Jovi had a hit single, "Who Says You Can't Go Home", with Jennifer Nettles of Sugarland. Kid Rock's collaboration with Sheryl Crow, "Picture," was a major crossover hit in 2001 and began Kid Rock's transition from hard rock to a country-rock hybrid that would later produce another major crossover hit, 2008's "All Summer Long." (Crow would also cross over into country with her hit "Easy.") Darius Rucker, former frontman for the 1990s pop-rock band Hootie & the Blowfish, began a country solo career in the late 2000s, one that to date has produced three albums and several hits on both the country charts and the Billboard Hot 100. Singer-songwriter Unknown Hinson became famous for his appearance in the Charlotte television show Wild, Wild, South, after which Hinson started his own band and toured in southern states. Other rock stars who featured a country song on their albums were Don Henley and Poison.

With the migration of many Southern rural whites to industrial cities during the Great Depression and World War II, country music was carried into new areas and exposed to new influences, such as blues and gospel music. The nostalgic bias of country music, with its lyrics about grinding poverty, orphaned children, bereft lovers, and lonely workers far from home, held special appeal during a time of wide-scale population shifts.
The music of Canada has reflected the diverse influences that have shaped the country.[1] Indigenous Peoples, the Irish, British, and the French have all made unique contributions to the musical heritage of Canada.[2] The music has subsequently been heavily influenced by American culture because of the proximity and migration between the two countries.[3] Since French explorer Samuel de Champlain arrived in 1605 and established the first permanent Canadian settlements at Port Royal and Québec in 1608, the country has produced its own composers, musicians and ensembles.[4][5]
Edward Balthasar Moogk (1975). Roll Back the Years: History of Canadian Recorded Sound and Its Legacy, Genesis to 1930. National Library of Canada. N.B.: In part, also, a bio-discography; the hardback ed. comes with a "phonodisc of historical Canadian recordings" (33 1/3 r.p.m., mono., 17 cm.) which the 1980 pbk. reprint lacks. ISBN 0-660-01382-7 (pbk.)
The idea of a band in country music had never really succeeded on a commercial level -- until Alabama kicked in the door in 1980. RCA rolled the dice on them, and it was an investment that paid off quite well –- over 30 No. 1 singles, 75 million in album sales, and the only band (so far) to win the CMA Entertainer of the Year award three times. To further underscore their success story, all of their singles for RCA in the 1980s -– save 1987’s “Tar Top” -- found their way to the pinnacle of the charts. 
Country music has been growing as an art from since Eck Robertson’s recording of “Arkansas Traveler” in 1922. From the days of 78 RPM vinyl to digital downloads, fans continue to flock to the format. So who are the 25 greatest country artists of all time? That list might very well be subject to conjecture as the definition of country, but here are the acts that have made an immeasurable mark on the genre. In compiling this list, we took into consideration sales, airplay, and influence upon the genre -- and outside of it. Let the debates commence! https://www.youtube.com/watch?v=JhZnhUiU448
Though some younger fans might not truly appreciate just what Eddy Arnold brought to the format, his down-home personality along with his slightly more sophisticated tone made him one of the format’s most bankable crossover stars. With a reign on the country top 40 that lasted for close to four decades, Arnold managed to keep a career going from the days of 78 RPM to the digital age.
While rappers like Dream Warriors and K-os were underground upstarts in the 90s to early 2000s, no Canadian artist was able to achieve mainstream popularity until former child-actor-turned-rapper, Drake, put Canada on the hip-hop map – becoming one of the biggest-selling and influential rap stars in the world. From co-founding Canadian record label OVO (October’s Very Own) Sound to coining the city’s unofficial nickname, “The 6”, Drake is Canada’s biggest hypeman. Not only did he use the CN Tower for his Views album art, he even has a tattoo of the iconic Toronto landmark on his arm and helped to introduce fellow Canadian, The Weeknd, to the rest of the world.

Canada has a long tradition of singer-songwriters and that’s partly in thanks to its own “folksong laureate”, Gordon Lightfoot. Coming out of the Toronto 60s folk music scene, Lightfoot’s native country would become his lifelong muse, penning such classics as ‘Canadian Railroad Trilogy’ and ‘Wreck of the Edmund Fitzgerald’ and yet universal enough to appeal worldwide, turning him into Canada’s most successful contemporary folk artist. A beloved cultural icon, he’s been the beneficiary of countless awards and honours including the Companion of the Order of Canada – Canada’s highest civilian honour.

Among the earliest musical societies were Halifax's "New Union Singing Society" of 1809 and Québec's "Harmonic Society" of 1820.[4] One of the first registered all-civilian musical ensembles was a religious sect organized from Upper Canada called the Children of Peace in 1820.[35] In 1833, a student orchestra was organized at the Séminaire de Québec the Société Ste-Cécile, as it was known, and was one of the earliest ensembles of its kind in Lower Canada.[35] The first appearance of a piece of music in a newspaper or magazine was in the pages of the Montreal twice-weekly newspaper, La Minerve, on September 19, 1831.[36] Many immigrants during this time lived in relative isolation and music sometimes obtained through subscriptions to newspapers and magazines, provided entertainment and a life line to civilization.[1] One of the earliest surviving publications in Canada of a song on the piano in sheet music format is "The Merry Bells of England" by J.F. Lehmann, of Bytown (later Ottawa) in 1840.[37]
Ultimately, country music’s roots lie in the ballads, folk songs, and popular songs of the English, Scots, and Irish settlers of the Appalachians and other parts of the South. In the early 1920s the traditional string-band music of the Southern mountain regions began to be commercially recorded, with Fiddlin’ John Carson garnering the genre’s first hit record in 1923. The vigour and realism of the rural songs, many lyrics of which were rather impersonal narratives of tragedies pointing to a stern Calvinist moral, stood in marked contrast to the often mawkish sentimentality of much of the popular music of the day.
Take a crew of Yes-obsessed Canadians, apply an English prog sensibility and you have one of the most successful rock acts to break out of Canada – selling over million records sold worldwide. Geddy Lee and Alex Lifeson grew up near Toronto and came up in the local club circuit before going on to form the illustrious prog-rock trio known as Rush. While the band’s sound would evolve over the years since their 1974 debut, their expert musicianship, complexity of their compositions and vivid lyricism would remain unparalleled. While Rush were the ones to hit it big, let’s not forgot other Canadian prog-rockers Saga, Klaatu and Triumph.
Significantly, however, the style occurred not in a city alive with the values of contemporary art but in Los Angeles, which during the previous decades had attracted many rural Southerners. Moreover, country rock’s rise to prominence paralleled the rise of the big-budget Hollywood recording studio ethic, the desire to compete with London in the effort to make pop recordings of the most highly advanced sonic clarity and detail then imaginable. Country rock had begun by insisting that the sources—and not the means—of popular music were of signal importance. Yet in the end the movement succeeded by adopting the same exacting production techniques pioneered by the Beatles and their producer George Martin.
These early styles had coalesced into a genre by the time the Illinois group Uncle Tupelo released their influential debut album No Depression in 1990.[93][94] The album is widely credited as being the first "alternative country" album, and inspired the name of No Depression magazine, which exclusively covered the new genre.[93][94] Following Uncle Tupelo's disbanding in 1994, its members formed two significant bands in genre: Wilco and Son Volt. Although Wilco's sound had moved away from country and towards indie rock by the time they released their critically acclaimed album Yankee Hotel Foxtrot in 2002, they have continued to be an influence on later alt-country artists.

During the 1930s a number of “singing cowboy” film stars, of whom Gene Autry was the best known, took country music and with suitably altered lyrics made it into a synthetic and adventitious “western” music. A second and more substantive variant of country music arose in the 1930s in the Texas-Oklahoma region, where the music of rural whites was exposed to the swing jazz of black orchestras. In response, a Western swing style evolved in the hands of Bob Wills and others and came to feature steel and amplified guitars and a strong dance rhythm. An even more important variant was honky-tonk, a country style that emerged in the 1940s with such figures as Ernest Tubb and Hank Williams. Honky-tonk’s fiddle–steel-guitar combination and its bitter, maudlin lyrics about rural whites adrift in the big city were widely adopted by other country musicians.
Not a bad list but where is Steppenwolf and Weeknd? Drake should be much higher on this list. He will easily go down as the most popular and talented artist in Canadian history despite what the critics (tradiitonal people) here might say. He is one of the only Canadian artists who has literally changed the landscape and direction of pop music and hiphop music. No other artist on this list did that on a grand scale
During the mid-1970s, Dolly Parton, a successful mainstream country artist since the late 1960s, mounted a high-profile campaign to cross over to pop music, culminating in her 1977 hit "Here You Come Again", which topped the U.S. country singles chart, and also reached No. 3 on the pop singles charts. Parton's male counterpart, Kenny Rogers, came from the opposite direction, aiming his music at the country charts, after a successful career in pop, rock and folk music with The First Edition, achieving success the same year with "Lucille", which topped the country charts and reached No. 5 on the U.S. pop singles charts, as well as reaching Number 1 on the British all-genre chart. Parton and Rogers would both continue to have success on both country and pop charts simultaneously, well into the 1980s. Artists like Crystal Gayle, Ronnie Milsap and Barbara Mandrell would also find success on the pop charts with their records. In 1975, author Paul Hemphill stated in the Saturday Evening Post, "Country music isn't really country anymore; it is a hybrid of nearly every form of popular music in America."[69]

The Kentucky band’s sprawling major-label debut did nothing to alter the independent spirit of singer-songwriter Jim James and his cohorts. The country-rock base retained elements of Memphis soul, classic ’70s rock and neo-psychedelic sounds, all drenched in salubrious washes of reverb. Besides, nothing says complete artistic freedom like 12 songs that average six minutes in length, many of which were recorded in a grain silo to give the reverb more reverb. Styles mix wantonly, songs meander but never go quite where you expect them to. What begins as an acoustic-driven folk song (“Magheeta”) morphs into a hard-rocking power ballad; a funkified homage to R&B clubs (“Dance Floors”) becomes an Exile on Main Street-era block party, powered by a propulsive horn section straight out of “Tumbling Dice”; and the minor-key melancholia of Neil Young’s Crazy Horse epics (think “Cortez the Killer”) forms the backbone of “Run Through” until it mutates at the chorus into the early ’80s Manchester sound reminiscent of New Order. Is it alt-country? That’s as good a descriptor as anything else.—John Schact
Wildly gifted songwriter who flies under the mainstream radar and is beloved by critics and musicians alike? Noticing a pattern here? Ron Sexsmith is another jewel in Canada’s singer-songwriter crown. With his distinctive and charming voice and wonderful melodic sense, he’s gained many famous admirers including Elvis Costello and Elton John. Sexsmith arrived in Toronto by way of St. Catherines and was praised for his songwriting since his self-titled, major label debut in 1995. After crafting 14 albums worth of earnest, guitar pop, Sexsmith developed a cult following despite many of songs becoming mainstream hits for others such as Feist’s ‘Secret Heart’ and Michael Buble’s Whatever It Takes’.
Authoring a song that would launch almost a 100 covers, ‘Hallelujah’ is just a small sliver of Leonard Cohen’s immense contribution to music over the past five decades. The accomplished poet and novelist was the toast of the Montreal literary scene before he turned to music to become the foremost songwriter of his era. His meditations on love, faith, despair and politics could be conveyed in even the simplest of terms. Songs like ‘Suzanne’ and ‘Bird on the Wire’ and ‘Sisters of Mercy’ would cement his reputation as a in-demand folk songwriter, spawning hits for countless other artists, but no one could replace Cohen’s deep, resonant voice.
1958 saw its first Canadian rock and roll teen idol Paul Anka, who went to New York City where he auditioned for ABC with the song "Diana".[78] This song brought Anka instant stardom as it reached number one on the US Billboard charts.[79] "Diana" has gone on to be one of the best selling 45s in music history.[80] US-born rockabilly pioneer Ronnie Hawkins moved to Canada in 1958, where he became a key player in the Canadian blues and rock scene.[81] The 4th of October was declared "Ronnie Hawkins Day" by the city of Toronto when Hawkins was inducted into Canada's Walk of Fame.[82] He was also inducted into the Canadian Music Industry Hall of Fame[83] and his pioneering contribution to rockabilly has been recognized with induction into the Rockabilly Hall of Fame.[84] https://www.youtube.com/watch?v=gtKVuwDQUl0
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