30. Dream Warriors
And Now The Legacy Begins (1991)
A global rap standard. This debut marries rap's time-tested best attributes - refined sampling, hard drums and an irreverent world view - with nerdy comic book references and true-to-life tales of growing up Jane and Finch. All in a rude-boy cadence that helped put this city's West Indian diaspora on the map.
The Double Cross (2011)
Although they hail from Halifax, Sloan have recorded most of their albums since relocating to Toronto. While the video for Everything You've Done Wrong (from 1996's One Chord To Another) featured a who's who of Toronto's music scene, including the Sadies' Dallas Good, The Double Cross is the sound of west-end maturity.
28. Handsome Ned
The Ballad Of Handsome Ned (1987)
While he didn't manage to release much music before dying of a heroin overdose in 1987, the Toronto alt country scene wouldn't be the same without his influence. This posthumous album perfectly captures a moment in Queen West history, just as that scene was about to blow up.
27. The Pursuit of Happiness
Love Junk (1988)
Awkwardly cool, with his long blond hair and oversized glasses, TPOH singer Moe Berg was, is, a Toronto icon. While the band's best-known song, I'm An Adult Now, was originally released as a single and re-recorded for Love Junk, Berg's knack for a power pop hook and forthright lyrics permeated the album.
26. Jane Siberry
No Borders Here (1984)
Most often remembered for the single (and video) Mimi On The Beach, the textured, often ambient No Borders Here proved that synthesizers don't have to be used to make soulless pop. Jane Siberry's Queen West artiness and carefully considered lyricism were unlike anything else on the radio.
25. Barenaked Ladies
The Yellow Tape (1991)
When the quirky Scarberian indie rockers Barenaked Ladies recorded this self-titled five-song demo tape as a calling card to take to SXSW, they were barely into their 20s. It sold like hotcakes off the stage and through word of mouth, and soon HMV and Sam the Record man wanted copies in stock. It became the first Canadian indie tape to go platinum and helped earn the group a major-label deal for Gordon.
24. Timber Timbre
A murky exploration of graveyard blues and ghostly folk, Taylor Kirk's third album as Timber Timbre captured our imagination and haunted our dreams. The stark minimalism is perfectly balanced by the subtly rich textures, evoking a haunted transistor radio playing odes to dead lovers.
Feel It Break (2011)
Katie Stelmanis impressed Toronto audiences with her breathtaking operatic vocals as a solo artist before she hooked up with Dorian Wolf and Maya Postepski. But once she discovered her theatrical flair, surrounded her chilly melodies with dark, electro-goth compositions and adopted the name Austra, she became much more than a local curio. We'll probably hear a lot more from the group, but it'll be hard to improve on this outstanding debut.
22. Death From Above 1979
You're A Woman, I'm A Machine (2004)
DFA1979 directed a frostbitten middle finger at practically everyone with this scabrous, sexed-up, sometimes sentimental guitar-and-drums album that prompted a pseudo-revolution in the minds of a generation of Canadian ne'er-do-wells - and near-riots upon Jesse Keeler and Sebastian Grainger's brief reunion at SXSW 2011.
21. Lowest of the Low
Shakespeare My Butt (1991)
Few albums conjure Toronto as it was 20 years ago as well as Lowest of the Low's folky, jangly debut. Singer Ron Hawkins painted vivid portraits of 90s Hogtown that made the Carlaw bridge, the Danforth's Only Café and taking the streetcar downtown seem like the most romantic things in the world.