2001

Various Artists—Gas CD (RAM Recordings/Select)

Toronto musician Chris Brown raided his Rolodex, dredging up some high-profile musical friends for this remarkably cohesive benefit album. Created to raise funds for protesters arrested at the Summit of the Americas in Quebec City last April, the disc ranges from spoken-word interludes by the likes of David Suzuki and Jello Biafra to the fierce political poetry of Michael Franti and Spearhead. Gas CD is at once immensely educational and enjoyable.—Tabassum Siddiqui

2002

K-OS—Exit (EMI)

The Toronto MC’s long-delayed, much-hyped debut was worth the wait. Sure, the guy’s all too aware of his prodigious talents, but when you can rap, sing, play and write as well as he can, it’s understandable. Exit is a genre-defying triumph—hip-hop with heart and soul. K-OS’s recent deal with influential U.S. label Astralwerks may finally open some eyes across the border to the renaissance in homegrown hip-hop.—TS

2003

Stars—Heart (PaperBag)

PaperBag Records got the ball rolling by giving us Broken Social Scene, but it was Broken’s Montreal/Toronto synth-pop pals Stars that they really had their eye on. Good thinking—the swoony quintet is much more immediately accessible than their art-rock counterparts, and Heart (their second full-length) revealed a band coming into their own unique sound. With fiery frontman Torquil Campbell playing Cupid to Amy Millan’s cooler-headed guitar goddess, it all added up to perfect, polished pop that sounded like falling in love.—TS

2004

Feist—Let It Die (Arts & Crafts)

Six years ago, I hosted a benefit show with several local singer-songwriters on the bill. My favourite singer at the time was a slip of a girl named Leslie Feist. A charming, unassuming guitar whiz with a drop-dead voice, she was slated to play last. By the time she and her band went on well after midnight, practically the entire room had cleared out. Fast forward to four weeks ago, when this hometown gal-made-good brought a 1500-strong crowd to its knees at the ridiculously packed Phoenix. Memo to those kids at C’est What (and every other microscopic, empty ramshackle room Feist ever played back then): Fuck you. While it’s a shame she had to move to Paris in order to find success, Feist deserves every last bit of it for Let It Die. Pouring her cabaret voice over a collection of velvet-upholstered cover tunes and tiny, perfect originals, she reminds us that the saddest part of a broken heart isn’t the ending, but rather the start.—TS

2005

Broken Social Scene—Broken Social Scene (Arts & Crafts)

You gotta root for your own, and if sprawling indie-rock collective Broken Social Scene has become somewhat of a local cause celebre, well, they deserve it. It couldn’t have been easy for them to shoulder the crushingly heavy expectations for their long-awaited (three years and counting) second record, but the hometown heroes rewarded the wait with a dense, difficult, and utterly beguiling work that reveals more of itself with every subsequent listen. Yeah, it’s a mess—a massive, layered, dramatic mess—but that’s the beauty of it. What other group would bury a K-OS cameo in swirls of sound and Leslie Feist’s hyperactive yelps (“Windsurfing Nation”)? Who else piles slivers of vocals and bits of blips on top of each other until the entire thing builds up to the point of collapse (the patented approach of BSS producer Dave Newfeld)? Half the time you haven’t the faintest idea what ringleader Kevin Drew is singing, and you realize you’re so deep into the music that you don’t even care, as when the vocals drop out of “Ibi Dreams of Pavement” before the entire thing bursts into a cacophony of horns. Art for art’s sake. A place for everyone and everything in its place. Glorious noise for an equally wonderful time in this city’s musical history.—TS

2006

TV on the Radio—Return to Cookie Mountain (Interscope)

Because first single “Wolf Like Me” was the best song of 2006, but also because this Bowie-approved NYC outfit has found the line between indie avant-garde and music that’s actually entertaining.—Jordan Bimm

2007

Radiohead—In Rainbows (Independent/XL)

The band’s best work since 2000’s Kid A, In Rainbows made headlines back in October for its unpredictable musicality and for its novel online release scheme, which allowed buyers to set their own price for the album’s 10 tracks. From the spastic, snare-heavy opener “15 Step” to the haunting comedown closer “Video Tape,” In Rainbows shows no shortage of creative accessibility—something especially evident on the album’s standout single “Jigsaw Falling into Place” and the downbeat gem “All I Need.” The best albums are perfect soundtracks to the season they are released in, and fall 2007 was all In Rainbows.—JB

2008

Vampire Weekend—Vampire Weekend (XL)

It was a good year to be a hyper-literate indie rock nerd, as a bunch of khaki-clad Ivy League grads took their obsessions with chamber pop and African music and recycled them into a sugary collection of three-minute pop ditties. From the opening strains of “Mansard Roof” to the collegiate exuberance of “Cape Cod Kwassa Kwassa” to the raging sock-hop of “Walcott,” Vampire Weekend summed up the sweetest parts of academic life, adding an assortment of references to faraway lands that you’ll long to explore after graduation. Their debut album was a simple, escapist pleasure, one that’s even more valuable when you’re trudging across a snowy campus, trying to differentiate Barthes from Descartes.—Rob Duffy

2009

We didn’t reach such an easy conclusion.