64. Grimes “Oblivion”
Electro-pop breakout Grimes pairs her chipmunk vocals, la la las and burbly beats, not to mention that adorable video, with dichotomously dark lyrics about the mental aftermath of a sexual assault.



63. Cowboy Junkies – “A Misguided Angel”
With “Sweet Jane,” the sexy and smoky first single the Cowboy Junkies’ debut album, The Trinity Sessions, the Toronto alternative folk band proved that they were good enough to cover a legendary band like The Velvet Underground. With their second single, the haunting and dreaming “A Misguided Angel,” they proved that they were even better when they played their own songs.



62. Danko Jones – “Cadillac”
This 1996 song from the Toronto rock trio is basically the Platonic Ideal of a Danko Jones song: naughty, boastful, bombastic, and bad ass with a killer rock riff and a refreshing lack of stereotypical Canadian meekness.



61. The Demics – “New York City”
This 1979 single from London, Ontario’s The Demics was named the greatest Canadian song of all time in Chart Magazine’s inaugural Best Canadian music poll in 1996 and was ranked fifth in a follow-up poll in 2000. In 2014, this punk ode to small-ish town frustration remains as vital as ever, and no Best Canadian Song list worth anything would be complete without it.



60. The Rheostatics – “Record Body Count”
This song from The Rheos’ beloved and critically acclaimed 1991 album, “Melville,” sees the Etobicoke, Ontario rock band at their strangest, most unique and most arresting. The short tune about about a suicidal young man named Joey remains a favourite of disaffected weirdos and art rockers the world over.



59. Bachman Turner Overdrive – “Takin’ Care Of Business”
It didn’t take long for Randy Bachman to make his mark when he split from The Guess Who in 1970. By 1974 BTO were an established band and “Takin’ Care Of Business,” their ode to getting things done, was a hard rock hit. Oddly, it was their song “You Ain’t Seen Nothing Yet” from next album “Not Fragile” that became an international number one.



58. The DeFranco Family – “Heartbeat It’s A Lovebeat”
In the early seventies, Canada had a pretty good reputation for folk music and a burgeoning reputation for rock, but the Great White North wasn’t really known for its boy bands and cheesy pop music. Port Colborne, Ontario’s DeFranco Family did their part to change all of that with this cheesy but catchy as hell ditty that hit number one in 1973 and landed the whole DeFranco family in Tiger Beat.



57. Esthero – “Heaven Sent”
Trip-hop gets a bad rap, which may be why rip-hop duo Esthero have ben laregly forgotten. The late-90s outfit’s best song, “Heaven Sent” mixed singer Esthero’s breathy, jazz-inflected and progressively tougher vocals over future Weeknd producer Doc’s impeccable quiet-loud production and turntable scratcing.



56. The Pursuit Of Happiness – “I’m An Adult Now”
This 1986 hit isn’t just a killer single that becomes more pointed and uncomfortably true with each passing year, it’s also one of the first and best independent success story in Canadian music history. In 1985, a little known band from Toronto recorded a song called “I’m An Adult Now,” filmed an extremely low budget video for it and released both by themselves. It became a massive hit and landed TPOH a record deal. Their debut album, “Love Junk,” went platinum in 1988.



55. 54-40 – “Baby Ran”
This track from 54-40’s eponymous second album was a breakthrough college radio hit for the Vancouver band in 1986. It remains the best 54-40 song that Hootie and the Blowfish never covered.



54. Poppy Family – “Which Way You Goin’ Billy”
The sweet and melancholy title track from The Poppy Family’s 1969 album was the Vancouver psychedelic pop rock band’s biggest hit. It was a number one single in Canada and Ireland, and reached number two of the US charts.



53. Michie Mee & L.A. Luv – “Jamaican Funk Canadian Style”
The godmother of Canadian hip-hop was the first northern rapper to sign to a U.S. label and be taken under the wing of an American star (KRS-One) and she did by representing the Tdot’s cultural mix with a healthy does of dancehall reggae as this classic single makes crystal clear.



52. Kathleen Edwards – “I Make The Dough, You Get The Glory”
Ottawa alt country singer/songwriter sings about eating at Toronto’s infamous Vesta Lunch diner, getting CBC airplay, and being more of a Marty McSorely than a Wayne Gretzky in this clever and thoroughly Canadian single from her critically and commercially successful 2008 album, “Asking For Flowers.”



51. Melanie Fiona – “It Kills Me”
This blistering and emotional track from Toronto’s Melanie Fiona topped cracked the Billboard Hot 100, earned a Grammy nomination for Best Female R&B Vocal Performance (the award eventually went to some up-and-comer named Beyonce), and established the singer as an R&B force on both sides of the border.



50. Zaki Ibrahim – “Draw The Line”
This striking and gorgeous lead track from Zaki Ibrahim’s 2012 album, “Every Opposite,” is a fine example of why the Canadian and South African soul and R&B singer garners so much praise, so many prestigious award nominations (including the Polaris 2013 short list), and opening slots for artists like Erykah Badu.