Her next two albums—the languid dreamscape Moon Pix (1998), and The Covers Record (2000), a stark, minimal take on artists like the Rolling Stones that often leaves its source material completely unrecognizable—furthered her reputation as an indie-folk visionary. Then came 2003’s You Are Free, a mixture of her quiet solo work pitted against traditional rock, which would be a worldwide hit. She even played the Letterman show, hunched over the piano with her hair covering her entire face in a buttoned-down shirt as big as a muumuu.
Success should have been cause for celebration, but Chan was breaking up with her first and only long-term boyfriend, and she threw her beloved Silvertone across a hotel room and smashed it. “It was either that or jump out the window,” she says. The tour didn’t help her stability. “In the morning I would go to the mini-bar and get Jack Daniel’s and do that all day long. Obviously, I was really unhappy, but I wasn’t goin’ to let myself know that, so I made sure I was drunk for every minute of every fuckin’ day. I was a mess. But again, it was the best time of my life. I don’t remember anything.”
It’s 10 a.m. on an overcast Wednesday, and Chan is by the pool at the Delano Hotel in Miami, wearing Blueblocker sunglasses from Kmart, sweatpants, and a plaid shirt. But when the sun emerges, she takes off all those things to reveal a blue pin-striped Louis Vuitton bikini.
After the You Are Free tour, Chan bought a one-bedroom apartment a few blocks from the hotel. Around this time, she also turned her cell phone off and ended communication with most everyone in her life (she hasn’t spoken to some friends in almost two years). This self-imposed isolation is extreme but seems to have served its purpose. Yes, she gets lonely sometimes, but solitude is where her songs come from. Chan doesn’t really write songs so much as channel them. “Usually, I just have a guitar,” she says, “and it comes out. The next day, if I remember it, then it’s a song.” No lyrics or chords (not that she reads music) are written down. Instead of realizing that this is an innate talent, a gift akin to her voice, Chan feels embarrassed by it. “It’s like a hobby,” she says.
The exception to her paperless writing method is “Willie,” one of the best tracks on The Greatest. “Willie” began when Chan took a three-hour cab ride to visit her grandmother in Florida. “The driver’s name was Willie,” Chan says. “He was an older gentleman. I was in a really good mood and trying to talk to him.” But he had no interest in conversation. Before their journey began, she went with him to drop something off with his girlfriend. They drove down a gravel road to a trailer that was surrounded by yipping miniature dogs. A woman came out, and “she was beautiful, with bleached-blonde hair and a white T-shirt and cut-off blue-jean shorts and barefoot. When she started coming closer, I could see his face changing and he got real happy.”
They ended up talking for the entire trip, and he told Chan about the ring he was going to give his girlfriend the next week. Chan’s guitar was in the trunk, but she had a pen and paper. “There’d be stretches when we weren’t talking, and I’d be singin’ the melody in my head, writing everything down. We’d stop to get gas and the song would still be playing in my mind.”
Chan’s earlier music was “triumphant” in the sense that it’s about survival, about self-exposure as an exorcism for shyness and upset and anger. On The Greatest, Chan can now show the beauty in love. Whether she has found it for herself, she knows it’s out there and aspires to it.
But there may always be times when, surrounded by the world, she prefers to think of herself in isolation. Next month, she begins a new tour and will be backed by many of the musicians who appear on The Greatest. The New York show will be on Valentine’s Day at Town Hall. With any luck, there won’t be a spotlight on her, so she can forget about all the lovers gathered in the darkness.
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