Songfacts®:

• Many of us have had a really cool babysitter at some point in our lives - one with long hair and interesting clothes and a little swagger. In this song, we find out that the cool babysitter has some issues, including a bad boyfriend. When Songfacts spoke with Dar Williams, she explained: "I met my babysitter again, when I was 23, and she told me that she'd had a less than perfect adolescence. When I wrote that song I was thinking about her, and then I was thinking about how I must have appeared to the kids I was babysitting for. I had a big thick biology book with a snake and a skull on it. And it looked so impressive. And what they didn't know is that I wasn't doing so well in biology and it's kind of a straightforward text. But I saw the way they saw me, and I remembered how I felt about my babysitter. And the early '70s were a special time. Although now that my kiddo - my son - has babysitters, I realize that that sort of long-haired babysitter with her little purse from Target and her little boots and her big earrings and her perfume, it's still much more mystical than your mom who hasn't taken a shower in four days. (laughing) And it's nice to see that continues to happen. It would be sad to think that golden era of hippie adolescence was just one decade of our history. I think I was that person, but I think that's what I see continuing."
• This is one of the most popular songs from Dar Williams' first full-length album, which she released after playing coffee shops and other small venues for a few years. It was first released on her own label, then picked up by Waterbug Records. In 1995, when Williams signed with Razor and Tie records, the albums was reissued and became a strong seller.