Week 538: “Chicago” by Sufjan Stevens (The Staves cover)

I’ve always felt a connection to the city of Chicago.

It’s probably because I’ve lived my whole life in Toronto, which, despite sometimes being referred to as the Canadian New York, is really more like the Canadian Chicago: big city on a Great Lake, nice skyline, with a maximum of one successful sports team at any one time.

Before we were married, my wife and I spent a few days in Chicago, and we loved it. While I was there, I couldn’t help wishing Toronto had some of Chicago’s characteristics. The beautiful waterfront. The rich architectural heritage. My grass-is-greener approach to being a tourist was silly for a couple of reasons: first, no city is perfect, and Toronto has plenty going for it. But second, Chicago has spent much of its own history admiring the greener grass of other cities.

Chicago’s old nickname, “The Second City,” dates back to the 1950s, and comes from its status as the cultural and economic second-place American city, perpetually overshadowed by New York. Even though the nickname is outdated (it’s now really the third city, with Los Angeles having passed it in importance several decades ago) Chicago still feels like a city that’s trying to live up to something, just like Toronto.

Toronto and Chicago are a bit like attention-starved middle siblings; not as cute as the baby, not as independent as the eldest, still trying to impress mom and dad by tying their own shoelaces or making ill-advised bids to host the Olympics.

Chicago may not be the subject of as many songs as New York, but it’s got a few, and this one is my absolute favourite.

What makes this a beautiful song:

1. The original version combines joy and nostalgia in a way that only Sufjan Stevens seems to have mastered.

2. The Staves translate the original indie orchestration into their patented three-part harmonies, simplifying the instrumentation and bringing the energy of the original down a few notches, all while maintaining the emotional impact.

3. As much as I love the way the three Staveley sisters’ voices blend, I do think that Jessica’s voice (she sings lead here, as she does in many of their songs) is my favourite. It’s incredibly pure and powerful, yet somehow modest and unassuming. Her voice is often featured in The Staves’ work, but it never feels like it’s overpowering the others. As it happens – and perhaps this is particularly relevant here – she is the middle sister of the three.

Recommended listening activity:

Celebrating second place.

Buy it here.