50. Jackie Mittoo
A founding member of the Skatalites and a Studio One mainstay, Jackie Mittoo was already a heavyweight in Jamaica before moving to Toronto in 1968. On Wishbone, he combined his reggae roots with R&B, soul and pop influences, producing a uniquely Toronto brand of organ funk.
49. Sandro Perri
Impossible Spaces (2011)
Sandro Perri's career spans experimental house music, breezy folk and jazz-inflected post-rock, but it wasn't until Impossible Spaces that he found a way to bring all those disparate influences together into a cohesive package. Wonderfully weird, yet still accessible and welcoming.
48. McKenna Mendelson Mainline
This Toronto blues rock band never fully achieved the international fame they flirted with throughout their brief career, but their grimy, amped-up sound played a huge part in how a generation of Torontonians came to love the genre.
47. Ian & Sylvia
Four Strong Winds (1964)
Canadian folk duo Ian Tyson and Sylvia Fricker (they married that year) were already making a name for themselves beyond Yorkville's folk revival scene when they released their sophomore album, Four Strong Winds, featuring original arrangements of traditional songs, an early Bob Dylan cover and (of course) the duo's Everly Brothersesque harmonies on their signature song, the title track.
46. Azari & III
Rare is the dance album that hangs together as beautifully as this ambitious debut from Toronto's pre-eminent gay-straight alliance. Born of the city's after-hours scene in the mid-00s, Azari & III's effusive reimagining of 80s house sleaze, 90s rave euphoria and eerie futuristic tech rumbles on with the adventurous zeal and dexterity of the best DJs.
Whale Music (1992)
Eccentric Etobicoke indie-rockers Rheostatics borrowed the title of a Paul Quarrington novel for their epic third album, Whale Music (not to be confused with the band's 1994 soundtrack to the film of the same name, which features their hit Claire). Many guests lent a hand on this musically adventurous, proggy and inspiring outing, including Rush's Neil Peart on drums. The album has been on Chart's list of greatest Canadian albums three times.
Soldiers Of Misfortune (1990)
Sacrifice proved themselves thrash metal pioneers with the 1990 release (and 1991 re-release on Metal Blade) of Soldiers Of Misfortune. Technical, dynamic, progressive and relentless - some call it the best thrash album despite its underratedness - it inspired many a Power Hour viewer to pick up a pointy guitar of his or her own.
Troubadour is mostly remembered for including the breakout smash Wavin' Flag, an uplift anthem that's since become a Coca-Cola ad disguised as a World Cup song, an all-star benefit single and a children's book. It was also the impetus for an ill-advised pop makeover - which K'naan recently apologized for in a New York Times op-ed - but there's a reason it caught fire. The album is the best distillation of the Somali Canadian's genre-stretching, adventurous take on conscious hip-hop.
42. Martha and the Muffins
Metro Music (1979)
With a British record deal, a hit in Echo Beach and Metro Music's cover designed by Peter Saville, Martha and the Muffins were never confined to the CanCon ghetto. The group's core was singer Martha Johnson and guitarist Mark Gane, but the original lineup, including sax player Andy Haas, shone with jazzy inventiveness.
41. Lenny Breau
Live at Bourbon St. (1995)
The Maine-born, Winnipeg-raised guitar virtuoso was a Toronto fixture in the 60s and 70s, and this two-disc package of live performances at the legendary local jazz club was recorded in 1983. Equally influenced by Nashville's Chet Atkins and flamenco greats, Lenny Breau plied his fingerpicking style on a seven-string guitar with a stride piano sensibility, working the bass as hard as the melody. He battled a heroin addiction much of his life, and died under mysterious circumstances in 1984. George Benson and Wes Montgomery have nothing on this immense talent.