20. Feist – “Mushaboom”
“1,2,3,4” got the iPod endorsement and the “Sesame Street” remake, but “Mushaboom” was Feist’s first proper introduction to the masses with that unique vocal style and a narrative about the pastoral fantasies of hipsters stuck second-floor living without a yard over playfully light instrumentation and a finger-snapped beat That manic pixie dream video didn’t hurt.



19. k-os – “Man I Used To Be”
The greatest inspired-by Michael Jackson track ever didn’t just jack the “Billie Jean” disco beat, it also lyrically put k-os into late MJ’s mindset. Its also a good reminder that Drake didn’t invent the skill of singing and rapping.



18. Bruce Cockburn – “Lovers In A Dangerous Time”
The post-9/11 era may have felt scary, but it had nothing on the terror of 80s Cold War when the end of the world truly felt nigh. That’s the subtextual background of this Bruce Cockburn classic, later covered beautifully by Barenaked Ladies, which gives the song much of its power. Lines like “Got to kick at the darkness ’til it bleeds daylight” don’t hurt, either.



17. Metric – “Hustle Rose”
Admittedly something of a deep cut, despite its former status as the band’s go-to encore, Hustle Rose might not be as well known as, say Dead Disco, but it should be. Perfectly capturing what makes Metric so special, the song starts off like an Anthems of a 17-Year-Old Girl sequel before settling into a finger-picked ballad and then exploding into an dance-rock epic soaring on a crunchy guitar, double-time drums and synths aimed squarely at the outer solar system.



16. Neil Young – “Harvest Moon”
Right around the time the music industry was painting Neil Young as the godfather of this newfangled “grunge” movement in 1992 he pulled a swerve and put out the decidedly not-grunge country album “Harvest Moon.” Young collaborators Pearl Jam have covered the title track during their shows.



15. Alanis Morissette – “You Oughta Know”
Long before every pop starlet broke free of her pop and/or Disney past with a racy new image and a leaked nude photo, Ottawa’s Alanis Morissette, formerly known as Alanis, ditched her neon crop tops and mall pop past with this blisteringly angry, confessional, and raunchy alternative hit in 1995. Dave Coulier has both confirmed and denied that he is the subject of the song’s woman scorned fury.



14. K.D Lang – “Constant Craving”
This single from cowpunk rebel-turned-grand dame of Canadian song K.D. Lang’s 1992 album, “Ingénue,” topped the charts in Canada, the U.S. and U.K and earned Lang a Grammy Award for Best Female Pop Vocal Performance and an MTV Video Music Award for Best Female Music Video. If imitation is, indeed, the best form of flattery, then The Rolling Stones flattered the crap out of Lang and “Constant Craving” with their 2007 song, “Anybody Seen My Baby?” The Stones later gave her and her songwriting partner a writing credit for the tune.



13. Baby Blue Soundcrew – “Love ‘Em All”
Before Drake’s OVO and its crew love, there was Baby Blue, a DJ collective that came out of the party and mixtape scenes. In 2001, they put out their second compilation album containing this criminally underrated gem featuring Can-Hop legend Choclaire and American rapper Mims. It’s a surprisingly street-focused club jam with an indelible pinging beat and anthemic rhymes showing up the haters with sheer dexterity.



12. Thrush Hermit – “From The Back Of The Film”
Joel Plaskett’s old band Thrush Hermit were victims of bad timing, having been signed to a major label after alt-rock’s mid-90s decline and then releasing their CanRock masterpiece “Clayton Park” just before the early-00s indie rock revival. But while that impacted sales, it didn’t affect songs like this East Coast neo-retro riff-rocker which to this day make me bummed out that they broke up.



11. Stompin Tom Connors – “Sudbury Saturday Night”
Late country legend Stompin’ Tom Connors’ ode to hard-living Northern Ontario miners remains one of his best known songs. Connors knew the north well, having scored his first big singing break at the Maple Leaf Hotel in Timmins, Ontario, home of Shania Twain.



10. Drake – “Started From The Bottom”
There is no bottom lower in hip-hop than the one reserved for a half-white, Jewish, Canadian child star, even if he grew up in a good neighbourhood, but “Started From the Bottom” isn’t Drake’s song anymore. It belongs to everyone now, and much like “Hold On, We’re Going Home” boasts his best singing turn, this is Drake in his fiercest rap form. We will be hearing this song forever.



9. Bryan Adams – “Summer of 69”
The meta nostalgia of Bryan Adam’s greatest hit runs deep–from “Got my first real six-string” onward, it inspires warm feelings for the 80s and the 60s, for any summer anytime, really. Despite its propulsive riffs and soaring guitar solos, it’s actually a bleak song about growing up and realizing that your dreams didn’t come true, that “nothing can last forever.” And yet this 1983 song somehow has, and that incongruity gives it an optimism it didn’t have at the time.



8. Gordon Lightfoot – “If You Could Read My Mind”
Orillia folk legend Gordon Lightfoot reached the top of the Canadian charts and the top 5 of the US Billboard Hot 100 in 1970 with this beautifully ponderous song, inspired by his divorce, from the album “Sit Down Young Stranger.” It’s probably the only folk song that sounds almost as good as a disco number.



7. Arcade Fire – “Rebellion (Lies)”
Arcade Fire have never been shy about crafting anthems, but none have been quite as anthemic as “Rebellion (Lies)” off their breakthrough debut album, “Funeral.” As the song gathers momentum, you can almost imagine Win and Regine leading an uprising against the liars-that-be.



6. The Band – “The Weight”
One of the best songs of all-time according to Rolling Stone magazine, this narrative tale from ’68 was inspired by Band member Levon Helm’s connection to the American Deep South. Artists from Diana Ross to Panic At The Disco to The Muppets have covered it.



5. Handsome Furs – “When I Get Back”
Taken from the electro-rock duo’s 2011 album “Sound Kapital,” the SOCAN Prize-nominated song “When I Get Back” chronicles a traveler’s need to find their way home even as it induces culture shock with its synthesized sound.



4. The Guess Who – “American Woman”
A North American number one hit for The Guess Who in 1970, this song has been interpreted as anti-American over the years, though songwriter Jim Kale denies that assertion. Lenny Kravitz’s 1999 cover of the song hit number three on the rock charts.



3. Constantines – “Nighttime Anytime (It’s Alright)”
Pitchfork considers Constantines 2003 album “Shine A Light” one of the best of the 2000s. The marquee track for the album was the urgent “Nighttime Anytime (It’s Alright).”



2. Leonard Cohen – “Everybody Knows”
Countless Cohen songs could have made this list, and many might call for would want “Hallelujah” or “Suzanne” but “Everybody Knows” it’s hard to deny Cohen as beat apocalyptic prophet. Presumably with a black turtleneck on, he pessimistically baritones that the boat is leaking, the fight is fixed, the good guys lost and the plague is coming over synth stabs and flamenco guitar licks.



1. Maestro Fresh Wes – “Let Your Backbone Slide”
First there’s that sample-n-scratch-bolstered breakbeat, which places the song in its historical era long before Maestro proclaims that “it’s 89 y’all, not Beethoven’s 5th.” Yet it sounds as fresh today as it did a quarter century ago, and can just as quickly fill a dancefloor.

Then there are the rhymes, a tough yet erudite demonstration that not only was Maestro “a hip-hop tic-tac-tician” but that he was “not American.” That may seem like an obvious line now, but back then Canadian rappers were loathe to admit such on wax in hopes of crossing over down south. Maestro stayed true to his northern roots, broke into the US top 40 anyway, and held the best-selling Canadian hip-hop single title for two decades. Yes, it’s still a throw down.