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Chan Marshall during a Cat Power performance at the Osheaga music festival in Montreal in 2008.Ian Barrett/The Globe and Mail

The indie artist Cat Power played Toronto venue History last weekend. Her current tour celebrates the 20th anniversary of The Greatest, her breakout album written during a calamitous, rock-bottom period.

“Once I wanted to be the greatest,” sang the Georgia native, who goes by Chan Marshall offstage. “No wind or waterfall could stall me.”

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Marshall’s vocals, slathered in reverb, rested at a lower register than they did two decades ago, a victim of gravity and a Marlboro lifestyle. Singing The Greatest – a country-soul expression of her boozy, romantic despair – was not just a performance of an album, but of a moment in time, she said.

The moment was bigger than hers alone. In 2006, indie artists such as Marshall, Jenny Lewis, TV on the Radio, Neko Case and Band of Horses (who are touring this year behind their 20-year-old debut album Everything All the Time) gravitated to the mainstream while the music business was in despair itself.

With the record industry wallowing at a low ebb caused by the shift to digital downloads from CDs, the indie-music revolution that began at the turn of the century peaked in 2006 with a flood of albums that represent a highwater mark of consequential music from liberated artists.

It can now can be seen as a golden age of indie music made by youthful, uncynical people. The hard realities and daunting odds related to maintaining a career music would come soon enough.

“Young people have less to lose,” said Justin West, president and chief executive officer of Montreal indie label Secret City Records. “They may be naive, but they do what they love to do.”

West says he started Secret City in 2006 because he had “nothing else going on,” and because no one would sign his high-school friend Patrick Watson to a record deal.

“People weren’t interested in what Patrick was doing. His music wasn’t pop and it wasn’t meant for radio.”

West released Watson’s debut album, the cinematic Close to Paradise, in the fall of 2006. The record no one else wanted went on to win the Polaris Music Prize in 2007.

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Patrick Watson, left, who leads the band named after him, drummer Robbie Kuster and guitarist Simon Angell perform at the Rivoli in Toronto in 2006.Jim Ross/The Globe and Mail

It was an odd time to launch a label: Music business revenues were tumbling year by year. The cause of the free fall can be traced back to June 1, 1999, when Shawn Fanning and Sean Parker founded Napster, the industry-disrupting file-sharing service that allowed users to download music tracks for free. The record companies that owned the music were ships boarded by pirates.

Major labels did not embrace the shift to digital. And while they had sued Napster into insolvency over copyright infringement by 2002, the digital genie had already been released from the bottle.

Despite the upheaval in the industry, however, mid-level artists thrived. Major labels were investing less in new talent, but they still lent marketing support and distribution to indie artists in addition to their own acts. The influence of radio and legacy media – the traditional music gatekeepers – was still important but waning. New taste-making online magazines appealed to young audiences: An 8.7 album review in Pitchfork could launch a career.

As could music placed in a television show. Watson’s profile, for example, was raised considerably when his song The Great Escape was featured in an episode of popular medical drama Grey’s Anatomy.

“It wasn’t pop hits getting all the placements in movies and on TV,” West said. “It was a time of independent curation.”

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Owen Pallett, who then performed as Final Fantasy, plays at the Polaris Music Prize gala in 2006 before being named winner of the inaugural prize.Dustin Rabin/Polaris Music Prize/Supplied

So, by the middle part of the decade, the industry was democratized, with vestiges of the powerful old systems still in place. It was something of a sweet spot for indie musicians, with the streaming services that would wreak havoc on artists’ incomes still unheard of.

It was in that environment that Steve Jordan, a former executive at Warner Music Canada, created the Polaris Music Prize in 2006. The annual award celebrates what its voters determine to be the best full-length Canadian album, based on artistic merit.

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Hawksley Workman in Paris in 2006, the same year he released the album Treeful of Starling.Alain Sacrez/Supplied

“The idea for Polaris occurred to me around 2002, when the indie explosion first started happening,” said Jordan, who stepped down as the prize’s executive director in 2020. “Artists like Arcade Fire and Feist and Broken Social Scene were realizing the route to audiences did not have to necessarily go through major Canadian labels.”

The prize is typically awarded to independent (and often esoteric) artists outside the mainstream. Final Fantasy (a.k.a. Owen Pallett) won the debut Polaris for the chamber-pop LP He Poos Clouds.

The giant novelty cheque for $20,000 Pallett received was aspirational. With a little entrepreneurial spirit and by the sweat of their brow, mid-level artists could still make a comfortable living.

“I could fly into the Winnipeg Folk Festival, put on a dazzling show, sell 400 CDs and fly home with a pocket full of money,” Hawksley Workman said.

The Juno-winning rocker released Treeful of Starling in 2006. He had fallen out of favour with his major label (Universal Music) and recorded the stripped-down album (about devolution, among other things) in the California desert.

“Goodbye to radio,” he sang. “Goodbye to the things that we’ve known.”

Workman was prophetic. The launch of Spotify in 2007 instigated a devastating decline in radio’s influence and, more importantly, in CD sales. The business of legal digital downloads on platforms such as iTunes was also doomed.

The golden age of indie music was over not long after 2006, a year that was glorious − some say the greatest.

Cat Power plays Montreal’s Beanfield Theatre, July 27; Calgary’s Palace Theatre, Aug. 7; Vancouver’s Commodore Ballroom, Aug. 10; Victoria’s Capital Ballroom, Aug. 11.

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Patrick Watson and his band around the time of their rise from unsigned act to Polaris Music Prize winner.The Canadian Press

Counting down 2006’s best pop, rock, folk, rap and electronic albums

25) Band of Horses: Everything All the Time (indie rock)

24) Lily Allen: Alright Still (pop)

23) The Tragically Hip: World Container (alt-rock)

22) Arctic Monkeys: Whatever People Say I Am, That’s What I’m Not (rock)

21) Destroyer: Destroyer’s Rubies (indie rock)

20) Rosanne Cash: Black Cadillac (Americana)

19) Junior Boys: So This Is Goodbye (electronic)

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Chan Marshall, who performs as Cat Power.Steve Gullick/Supplied

18) Patrick Watson: Close to Paradise (art rock)

17) Joanna Newsom: Ys (indie folk)

16) Clipse: Hell Hath No Fury (hip hop)

15) The Hold Steady: Boys and Girls in America (indie rock)

14) The Dears: Gang of Losers (indie rock)

13) Neko Case: Fox Confessor Brings the Flood (country soul)

12) Hawksley Workman: Treeful of Starling (folk rock)

11) The Decemberists: The Crane Wife (prog/indie rock)

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10) Sonic Youth: Rather Ripped (alternative rock)

9) Justin Timberlake: FutureSex/LoveSounds (pop/R&B)

8) The Knife: Silent Shout (electronic)

7) Gnarls Barkley: St. Elsewhere (psychedelic soul)

6) Jenny Lewis and the Watson Twins: Rabbit Fur Coat (Americana/soul)

5) Bob Dylan: Modern Times (rock)

4) TV on the Radio: Return to Cookie Mountain (art rock)

3) Ghostface Killah: Fishscale (hip hop)

2) Amy Winehouse: Back to Black (pop/R&B)

1) Cat Power: The Greatest (indie country/soul)