Singer-songwriter Sarah McLachlan. (Sony BMG Canada)

In 1997, I bleached a blazing fuchsia streak into the front of my bangs in homage to Sarah McLachlan. The singer-songwriter had just transformed her pre-Raphaelite mane into a cropped coiffure with a punky pink cowlick for the launch of her fourth studio album, Surfacing. By dyeing my hair, I thought I was conveying my dissatisfaction with the status quo. Little did I know I was modelling myself on one of the savviest businesswomen in contemporary music.

This past week, McLachlan released Closer; it’s the first greatest-hits compilation of her two-decade career, though you can be forgiven for thinking she’s been down this road before. Since her debut album, Touch (1988), McLachlan has released 18 full-length albums — 19, if you count the online-only iTunes Originals from 2006— yet only five of them are proper studio albums of new material. The rest are a dog’s breakfast of covers, seasonal ditties and countless remixes and alternate takes of existing tunes.

At the apex of my teen angst, I found solace in McLachlan’s music. With lilting ballads about unrequited love and isolation, Solace (1991) was the first McLachlan album to strike a chord with me. I preferred it to Touch, though I still appreciated the ethereal vocals and mystical melodies on that earlier release. Fumbling Toward Ecstasy (1993) came out just before my 13^th birthday, and it floored me. It was a tumultuous sea of ambient keyboards, filigreed guitar work and complicated vocal runs, fused with a combo of brushed percussion and programmed beats. McLachlan’s lyrics were overwrought and bloodied; she wallowed in despair and yearned for redemption. A self-described outcast, McLachlan became a voice for kids who hovered between subcultures — she mixed the ominous gloom of the goth scene with the quirkiness of new wave and doused it all with fairy dust.

McLachlan performs her hit Fallen at the 2004 Grammy Awards in Los Angeles, Calif. (Frank Micelotta/Getty Images)

Even today, Fumbling Towards Ecstasy stands up. Surfacing was a bigger commercial success, and I’d argue that it marks the moment where McLachlan lost the program. I’m mortified to admit this now, but at a CD signing in 1997, I gave McLachlan a copy of Le Petit Prince inscribed with a seven-page treatise on how her songs had saved my life. (No, really.) Ironically, my heartfelt gesture coincided with the Vancouver-based singer-songwriter’s transition from artist to brand.

That season, posters for Surfacing (featuring the singer’s flame-streaked ’do) seemed to cover every available surface in downtown Toronto. McLachlan did innumerable radio interviews and endured meet-and-greets with eager fans in record outlets. That summer, she also launched Lilith Fair, her touring, all-female road show. Surfacing went on to sell millions of copies – it was certified eight-times multi-platinum in the United States and 10-times platinum in Canada – while Lilith Fair would last three years and leave more than 10 Women & Songs compilation CDs in its wake.

On Surfacing, her enigmatic lyrics and circuitous, soaring melodies were replaced with ponderous, maudlin piano ballads like Adia and Angel and radio-friendly hooks. Even the album’s few interesting songs (like the gospel-lite Witness) felt toothless. Many of McLachlan’s hardcore devotees agree. “Where has the real Sarah gone?“ reads one of the FAQs on the now relatively dormant Fumblers fan site. The post notes: “Many long-time fans feel that there is a quite noticeable change in Sarah’s music, and not a change for the better, after the material which appeared first on the album Fumbling Towards Ecstasy.”

So what happened? For one, Fumbling set the bar too high. The passion it generated among her fans was daunting – especially for someone who, by her own admission, regularly battles writer’s block. It took McLachlan three years to release Surfacing. In the interim, she fell in love and got married (to drummer Ashwin Sood, from whom she separated earlier this year). Genuine happiness rarely bodes well for artists who write anthems of angst, but I think that the watered-down tone of the songs on Surfacing and its predecessor, Afterglow (2003), has more to do with self-doubt. Rather than try to satisfy weirder fringe fans, McLachlan decided to target a middle-of-the-road demographic with material that was eminently more marketable.

You can also cast some blame on Lilith Fair. McLachlan not only became the poster girl for a cozy cardigan brand of pop feminism, she was seen to be putting her career on the line for the sake of this girl-powered pipe dream. But Lilith seemed to open McLachlan’s eyes to the power of branding. It seemed to me that public interest in the tour had less to do with specific acts than with the idea of an ideological group hug — from body glitter to pore-cleansing strips to literature on domestic violence, any concept that smacked even slightly of girl power hitched its wagon to the Lilith caravan.

McLachlan wins a Juno award for Songwriter of the Year at the 2004 Junos in Edmonton, Alta. (Carlo Allegri/Getty Images)

After that, McLachlan morphed from a tormented artist into a sort of cottage industry. She had already worked out a smart deal with her forward-thinking record label, Nettwerk, in which she owned the rights to her master tapes. (It meant that she would receive greater profits from reconfiguring previously released material than if she had signed a traditional deal with a major label.) McLachlan also wised up to the wonders of merchandising. Those earth mamas who bought Lilith tickets went nuts when McLachlan collaborated with her touring chef on a pesco-vegetarian cookbook with the corny title Plenty (in honour of a song on Fumbling Towards Ecstasy).

Most cannily, the singer-songwriter figured out that if you throw in one or two unreleased snippets on a collection of dusty old tunes – as she does with the pair of tepid breakup ballads on Closer – fans will shell out just as much as they would on an album of entirely new material.

My own love affair with McLachlan tapered out years ago, likely around the same time I let my original hair colour grow back in. I haven’t been able to stomach any of her post-Surfacing work — the tracks on Afterglow, for example, show how the vivid, Hieronymous Bosch-like imagery of yore has become a flaky mess of platitudes. Yet as I scanned the track listing of Closer, I was overcome by melancholy. I know that part of that feeling has to do with basic nostalgia. But on a deeper level, I think the old, awestruck teenager in me misses the way it felt to be a super-fan – and that kid feels kind of let down.

Closer is in stores now. McLachlan will be featured on CBC Radio One's arts and culture show Q on Oct. 17, doing an exclusive performance at the Glenn Gould Studio.

Sarah Liss writes about the arts for CBCNews.ca.