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.

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.