49. Bran Van 3000 – “Drinking In L.A”
In 1997, an electro-alterna-rock collective from Montreal called Bran Van 3000 came out of nowhere and conquered the Canadian (and U.K.) airwaves with the irresistibly infectious “Drinking In L.A.” It remains the single catchiest pop song that has ever been written about ennui and career dissatisfaction.



48. Men Without Hats – “Safety Dance”
We have a real-life “Footloose” situation to thank for this ubiquitous new wave hit from 1983. Singer Ian Doroschuk wrote “Safety Dance” after getting kicked out of a club for pogoing.



47. Joni MItchell – “A Case Of You”
This classic from the 1971 album “Blue” sees Alberta’s folk giant Joni Mitchell at her most poignant and piercing. Given that Mitchell is responsible for an entire career’s worth of poignant and piercing songs like “Free Man In Paris,” “People’s Parties,” “Both Sides Now,” “Big Yellow Taxi,” “River” and “Woodstock,” that’s saying quite a lot.



46. Rough Trade – “High School Confidential”
This unflinching and unsentimental look at teenage sexual frustration from the Toronto new wave band Rough Trade’s 1980 album “Avoid Freud” became one of the most sexually explicit songs to ever appear on the Canadian pop charts when it cracked the top 20 the following year. The lyrics, even the infamous “She makes me cream my jeans when she comes my way” line, might be borderline tame by today’s standards, but the song remains every bit as cool as the day it was released.



45. Jann Arden – “Could I Be Your Girl”
The sweet, melodic melancholy of this 1994 single from Calgary’s Jann Arden makes the singer’s biggest hit, “Insensitive,” look positively perky by comparison. “Could I Be Your Girl” took home the Single Of The Year Juno in 1995.



44. Sarah McLachlan – “Good Enough”
“Good Enough” was the third single from Sarah McLachlan’s 1993 breakthrough album “Fumbling Towards Ecstasy.” That album would sell almost three million copies in the U.S.



43. Ian and Sylvia – “Four Strong Winds”
CBC Radio listeners voted this the best Canadian song of all time in a 2005 poll for 50 Tracks: The Canadian Version, and with good reason. The iconic sixties folk classic by Toronto’s Ian and Sylvia remains one of the most beautiful and heartbreaking things to ever come out of this country. And the covers – by the likes of Sarah McLachlan, Hank Snow, Johnny Cash, John Denver, Neil Young and many more – are all pretty swell, too.



42. Death From Above 1979 – “Romantic Rights”
“Romantic Rights,” the first single from Death From Above 1979’s 2004 debut “You’re A Woman, I’m A Machine” was a perfect introduction to the Toronto duo’s doing it-themed noise rock. As happy as we are about the band’s reunion and upcomiong second album, we have problems believing that anything could ever top this.



41. Dream Warrior – “My Definition Of A Boombastic Jazz Style”
There’s something uniquely Canadian about sampling the theme music from a nerdy CTV game show for your hip-hop track. Which is exactly what Toronto’s Dream Warriors
did with the theme from “Definition” (“Soul Bossa Nova” by Quincy Jones) on this massive jazz hip hop hit from 1991.