Amos explained this song in an interview with Amazon: "As a woman it's hugely important to know what you're attracted to and just to be honest with yourself about it. Because the song 'Ophelia' is about a woman who is drawn to situations - I would say not just men but situations - where somebody needs to have control over her in some way, and she hasn't been able to break the chain of these people. They seem to come in different forms in her life. So until you yourself begin to know, Why am I attracted to people who are like this? then you can't break free. Sometimes you're not willing to look at this characteristic in them; you're not willing to see it for some reason. And that's the story of 'Ophelia.'"
Amos explained in publicity materials how this song's subject matter connects with the album title. She said that the song "is about choosing to be with someone who doesn't respect you and doesn't value you. That leads us right back to what sin really is. What is sinful? It's not what the church says to me is sinful. It's me degrading myself, or somebody else wanting to degrade me and me allowing it to happen. We, as women, could choose to walk away from so much of what's going on, but it seems as if we're not making that choice, and I'm asking myself all the time 'Why? What have we, the older generation of women, not done?' Who would have thought that we could regress to this point?"
The album title is borrowed from a line spoken by Jean Simmons as Sister Sarah Brown in the 1955 musical Guys & Dolls. Brown, a member of the Save a Soul Mission that opposes gambling, tries to convert high-stakes gambler Sky Masterson (Marlon Brando).
The music video, directed by Christian Lamb, finds Ophelia wandering a graveyard as a masked woman stalks her (both roles are played by the singer). Amos explained the genesis of the clip:
"'Ophelia' is a song that came to me later on in the project and I was traveling again, and when the music came I really wanted to represent this filmatically in a graveyard. So when Christian and I were talking about graveyards, he had people scouting in New Orleans. These are two different graveyards that you're seeing, and the one that seems to be as big as Manhattan, it has - my god – temples; the graveyards, the graves themselves, some of them are bigger than people's living space.
It's something that she's denying... that's stalking her in a way, represented by the masked lady - that which is hidden but it demanding to be addressed. The fact that she's hiding between death so that she doesn't have to look at real-life events intrigues me in a way. Stepping into these different points of view at different times of the day was intriguing to me because there was such strength being the masked woman who seemed to know the secrets and then stepping into the woman that has been avoiding looking at the depth of a certain story in her life. And only until she looks at it can she stop the pattern, stop repeating it in different ways in her life. She's a destructive character, and that's why she's gotta break the chain - and yet, it is a choice isn't it? If you're attracted to destructive situations, then how do you break that attraction? That's the key. If she's able to kind of go back to those pivotal points in her different relationships where she almost gets a high out of hurting herself, she becomes addicted to it, then she can get to a place where she's not attracted to it anymore. But she's not there yet. And that's why I think the other woman is taking her to a point of view looking at her involvement in it. She's not just a victim anymore, our Ophelia. She seems to be drawn to these really demeaning relationships and situations."
This was Amos' first album after a three-album stint with Epic Records. She signed a joint-venture agreement with Universal Republic that allowed her to retain control over her vision for the album, which ended up being an audio-visual project with a series of short films ("visualettes") to supplement the songs.