The 10 Hottest Singer-Songwriters of the '90s

The sexiest sensitive songbirds of the Clinton era: The 10 Hottest '90s Singer-Songwriters

Complex Original

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Ah, the '90s. What a strange time in music. Among the flurry of unshowered grunge bands (Nirvana and Nine Inch Nails) and backwoods-festival-playing alternative rock groups (Counting Crows, Hootie and the Blowfish, Dave Matthews Band and The Wallflowers), were a few ladies with acoustic guitars and pianos and a closet full of bones to pick with the male of the species.

From Lisa Loeb, who's releasing her latest album, No Fairytale, today, to Alanis Morissette, female singer-songwriters came out with the message that girls rock too, girls don't need boys to rock, girls can do their own damn summer music extravaganza and name it Lilith Fair and boyfriends will have to go. And go they did, those '90s boyfriends.

Here are the 10 hottest female singer-songwriters of the '90s. And for the record, they didn't all play Lilith. Just seven out of 10—Lisa Loeb included.

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10. Tori Amos

Greatest hit: "God" (1994)

Tori Amos arguably was the original female singer-songwriter of the '90s, getting the jump on many of the gals by releasing her first singles in 1991 (from the 1992 album Under the Pink) and peaking creatively with Boys for Pele in 1996. She was the gateway drug of ladymusic.

9. Natalie Merchant

Greatest hit: "Carnival" (1995)

Merchant was a star waiting to happen as the lead singer and songwriter of 10,000 Maniacs, and when she struck out on her own with Tigerlily in 1995, there was a sense that we'd get more Natalie than ever before. Unfortunately, her solo career was musically mediocre, and even though it was her name on the record, she never asserted herself as "Natalie, the glamorous star."

She could have, though. In mid-'90s photos, she has this look like she is about to turn up the sexy like talented people sometimes do. But she never has. Cute Natalie Merchant and Serious Natalie Merchant are ever-present, but Sexy Natalie Merchant remains a fantasy.

8. Alanis Morissette

Greatest hit: "You Oughta Know" (1995)

Alanis Morissette was a music industry veteran, having released two successful dance-pop albums in Canada as a teenager. It follows, then, that her breakthrough album, Jagged Little Pill, was more of a rockin' affair than those put out by the typical Lilith girls.

But don't be misled by the slick vocals and polished production. Alanis wrote every lyric on the album and co-wrote all the music. Despite Jagged Little Pill's humongous pop success—33 million units moved worldwide and four Grammys —Alanis has singer-songwriter DNA.

7. Sarah McLachlan

Greatest hit: "I Will Remember You" (1995)

As McLachlan continues to be more prolific with her BC SPCA End Animal Cruelty campaign commercials than her music, it's getting harder to remember that she was arguably the queen bee of this singer-songwriter swarm. There was no defending a Sarah McLachlan CD in your collection: At best, you were borrowing it from your girlfriend, and were totally whipped, and at worst, you genuinely liked it and were Mr. Sensitive Ponytail Guy.

But what sets McLachlan apart is that she, more than any of her peers, realized that this was not just a trend, it was a movement. She founded Lilith Fair in 1997 and the devotees, clad in tank tops and Birkenstocks, showed up in droves.

6. Lisa Loeb

Greatest hit: "Stay (I Missed You)" (1994)

In 1994, Lisa Loeb was an unsigned musician living across the street from Ethan Hawke. It out to be a good thing if you've got a catchy tune to sing and you're kinda hot in a naughty librarian way. Hawke helped to get Loeb's song into the Gen-Xploitation flick Reality Bites, and he also directed the one-take video that made her famous. Suddenly everyone wanted to be having a tortured conversation with a girl in a little dress and kittycat specs.

5. Sheryl Crow

Greatest hit: "All I Wanna Do" (1994)

Sheryl Crow had been around the block a few times before finding success. She had sung backup vocals for Stevie Wonder, Belinda Carlisle, and Don Henley, and toured as a backup singer for Michael Jackson, circa Bad. Perhaps that's why her songs had a certain emotional maturity that others didn't; you didn't feel like you were arguing with your girlfriend when you listened to a Sheryl Crow album. That is a good thing.

Sheryl was also not afraid to be sexy. She had always wanted to be a rock star, and when she found herself having her moment in the early '90s, she gladly embraced her sex-symbol status.

4. Jewel

Greatest hit: "Who Will Save Your Soul" (1996)

Jewel was 21 when she recorded Pieces of You, her debut album, and like so many of these (then) young ladies, you didn't quite know what to make of her. You might not have bet money back in 1995 that young Jewel Kilcher, baby-faced and super-sensitive, would end up the sex symbol of the bunch. But there she was just a few years later, brimming with confidence and busting out of her corsets.

3. Liz Phair

Greatest hit: "Supernova" (1994)

Phair is a singer-songwriter who really just wanted to be a rock chick. Her natural instrument is the electric guitar and her voice is usually described as a monotone. It's a far cry from the coffehouse acoustic sounds and soaring vocals that became the sound of the mid-'90s.

But then, Liz was a little earlier, releasing Exile in Guyville in 1992 and announcing to the world (in "Flower," the song nobody forgets) that she would be its blowjob queen. Phair always got a lot of attention for her potty mouth and physical beauty.

2. Natalie Imbruglia

Greatest hit: "Torn" (1997)

Natalie Imbruglia came in during the last third of the decade, a hot pistol out of Australia with a mega-hit single in "Torn." She did not write "Torn"—it was a cover of an Ednaswap tune—but she co-wrote 10 of the 12 songs on her 1997 album Left of the Middle.

Is it fair to include her on this list? After all, prior to her singing career, she was as an actress on the Australian soap opera Neighbours, a job she got at least partially because she is supernaturally beautiful. If this list is the singer-songwriter table in the junior-high cafeteria, the other nine of them would not be too stoked about Natalie having a seat. But we'd give her the benefit of the doubt and say she's down for the cause.

1. Fiona Apple

Greatest hit: "Criminal" (1997)

Fiona was the naughty little girl among singer-songwriters, debuting at the tender age of 18 and dressing provocatively in the video for "Criminal."

"I decided if I was going to be exploited, then I would do the exploiting myself," she later said of the clip. It was one of many candid statements that gave Fiona a much different reputation than the Lisa Loebs and Sarah McLachlans of the scene.

When she accepted her MTV Music Award for Best New Artist, she told the crowd, "This world is bullshit, and you shouldn't model your life on what we think is cool, and what we're wearing and what we're saying." Which cemented her status as the hottest rebel of the decade.