Sheryl Crow and Lance Armstrong on Life and Love

Sept. 16, 2005 — -- Sheryl Crow and Lance Armstrong are an uncanny match. Each seems to have done the impossible professionally. Armstrong beat cancer to become the best cyclist in the world, with an unprecedented seven victories in the Tour de France, and Crow is among the few elite women to have maintained a solo music career past the age of 40.

The couple, who have been an item for about two years, just this month announced their plans to marry in the spring. But their journey to this point has been a long one.

While Crow says she had a typical childhood growing up in a close-knit family in Kennett, Mo., her music reflects a feeling for the darkness and drama lurking beneath everyday life.

She described that melancholic sensitivity in her music to "20/20's" Elizabeth Vargas. "Each household has its certain amount of chaos -- just trying to keep all the plates spinning. But even deeper than that, there's just so much chaos in the world, and it does affect each of us spiritually," she said.

"She goes really beneath the surface of things," said Tamara Conniff, executive editor of Billboard magazine. "She filters the pain that she sees in the world and the pain that she's seen in her own life," Conniff added.

And while her breakthrough 1993 hit "All I Wanna Do," had a lighthearted hook to it, there was still that tinge of world-weariness that's a signature of Crow's work. The single brought her the first of her nine Grammys.

When Vargas spoke to Crow in 2003, she said her life was, in fact, an isolated one. "The work has made me lonely because writing is lonely," she said.

Finding the Right Kind of Love

But a lot has changed in the two years since Vargas last interviewed Crow. "I've always wanted to be in a relationship that felt supportive and elevating. And I've also always wanted to be that for someone else," she said.

And Crow seems to have found that sort of relationship with Armstrong, who she met by chance at a charity event hosted by tennis great Andre Agassi in the autumn of 2003.

She's not one to open up about her romantic relationships, but she's described Armstrong as her soul mate. "I've been so private about my private life and so protective. And for me to actually do an interview with a person I'm involved with is like a huge stretch for me," she said.

She made that stretch when we sat down with Sheryl and Lance together.

Armstrong -- who has a son, Luke, and twin daughters, Grace and Isabelle, from his first marriage -- knows the pain of being in a relationship that's falling apart. "Relationships are tough. They're a heck of a lot tougher than the Tour de France," he told Vargas.

Many of Crow's fans questioned her decision to put her own career on hold to support Armstrong during a difficult two years that included his divorce and his successful bid to win his seventh Tour de France title.

"She's come along and supported me as a man, as a person. The last couple of years of my life haven't been stress-free. There's been bumps along the way on the road -- going through a divorce, having three small children that are in Texas and my sport is based in Europe. So having Sheryl there to help me was huge," he said.

Crow said some of her fans thought she was making a mistake by setting aside her own career for a man.

"There are people who still think I'm nuts. I mean I have a massive feminist following. And a lot of those people are mad. They're like, 'Why would you quit everything for a man?'" she said.

But Crow said she has no regrets. "It was a choice. And I really gave myself the gift of just saying, 'I can do whatever I want. I can follow this person around and just wash his bike shorts if I want.'"

She's also quick to point out that her past year hasn't been all Lance, all the time.

Over Memorial Day weekend, Crow was on her own emotional journey.Her hometown of Kennett, Mo., was dedicating the Sheryl Crow Aquatic Center, a town swimming pool she'd been instrumental in funding.

The weekend festivities included a Sheryl Crow concert … complete with her father in the backup band.On the program was a song called "My Favorite Mistake." It's a song rumored to have been about Crow's relationship with Eric Clapton. She's called it one of her personal favorites.

"That song was just one of those songs that came together really easily," she said. "The best you can hope for is to feel like you got out of your own way and wrote something that was pure," she added.

'We're Simple, Local People'

So, who was the mistake? She wouldn't offer more than, "It doesn't matter."

Armstrong's favorite song from his fiancee's musical catalog, "Home," springs from a much less ambiguous source of inspiration.

Lance says the video's nostalgic hometown images really resonate for them."At the core, we're both very simple, local people. We're not people that enjoy the high life. We would much rather be at the house in shorts and a T-shirt. So, ultimately, your home is your home, and it's the safe haven and to escape," he said.

Escaping attention hasn't been easy for the couple, especially when Lance won his seventh Tour De France in July with his children and Sheryl Crow at his side.

And that's difficult for Crow. "It's just, for me, a terrifying place to be and it really does take its toll on your relationship, no matter how much you can joke about it. What gets written about you can be very destructive," Crow said.

It must have felt particularly trying at the end of August when a French magazine rekindled old -- vehemently denied -- accusations that Lance was using steroids during the 1999 Tour De France.

The charge frustrated Armstrong so much he said he might leave retirement and compete for his eighth victory, just to get even. But Thursday, he confirmed he would not compete again.

That competitive drive is the battling instinct he used to fight cancer. He says it comes from his mother. "She grew up a fighter. And since she was 17 when she had me, we grew up fighters. It's a fighting mentality which especially served me well when I was sick and I suppose still serves me well to this day," he said.

A New -- Happier -- Influence on Her Music

As Crow has become part of Armstrong's life, she's developed a relationship not only with him, but with his three children. Her closeness with the kids was evident in photos of her holding them as Armstrong celebrated his victory in Paris.

"They're small and they're precious and I strongly attribute it to both their father and their mother," she said.

Being a mother herself was a strong desire Crow had when she last visited with "20/20." And it still is. "I would love to have my own kids, and I think that I will," she said.

She said she loves Armstrong's children like they were her own. "It's been fun for me, and a new thing, to not be in my little selfish me world."

Crow's new world is reflected in the album she's releasing later this month, "Wildflowers."

Critics who've heard it say they can spot the changes and the influences.

"I think the Lance influence on Sheryl is happiness. She's really gone through a lot when it comes to love, and he's really centered her and allowed her to focus on what's important to her as an artist," said Conniff.

Crow certainly spots the influence herself. "I've never had anybody be so completely positive that I'm the person that they want to be with. That's helped me express who I really am and who I can be."