As a teenager, I was a huge Cyndi Lauper fan. I loved her music, wanted to look like her, and for a year or so in high school, modelled my wardrobe after the outfits from the videos for her album She’s so Unusual.

By the late 80s though, I had moved on to other types of music and didn’t keep up on everything Cyndi. One night in the summer of ’88, when I was living in Kensington Market, we came home fairly late to find that the streets were blocked off for a film set. This was the summer of that bad vampire detective show Forever Night, which seemed to be filming everywhere in Toronto at the time, so we assumed that’s what it was, and went a few blocks out of our way to get home.

In the middle of the night we woke up to the same Cyndi Lauper song playing over and over again. It was a song I didn’t recognize but as it was a hot night my roommate Amanda and I left the door to our little attic balcony open to catch a breeze. Restlessly we fell asleep to the sound of Cyndi singing. The next morning, the whole market was abuzz about the Cyndi Lauper video shoot that had taken place the night before. Yep, Cyndi Lauper has been right there, on my street, and I had missed her.

This is a trend that, 20 years later, has not changed. Lauper has toured and come to Toronto a number of times and I’ve always missed her, for a variety of reasons. So when they announced the line-up for the Pride stage this year and that Lauper would be doing a free concert, I was obviously chuffed. I was finally going to get to see her perform live.

We arrived an hour and a half before she was supposed to take the stage and the venue was already packed. Taking place in a huge downtown park, the Pride organizers had fenced off the entire event area so the whole thing could be licensed. Which is nice, but not if it requires waiting an hour in line to get through a bag check. We peered through the fence behind a food vendor and assessed the crowd. The area in front of the stage was already packed solid. Even if we got inside before she went onstage, we’d never actually get to see her.

It wasn’t meant to happen.

We had been cranky about the fact that Lauper was performing at the same time as the final event of the Toronto Jazz Festival, which was a performance by Chaka Khan and Macy Gray. So we gave up trying to see Cyndi and headed down to Yonge Dundas Square. It was less packed than it had been a couple of weeks before for Iggy and the Stooges, and we quickly got into the beer garden where there was much more room to move around. We still couldn’t see much of Khan (except for her massive hair), but she sounded amazing. The mood of the crowd was really wonderful – people were dressed up, and there were Grandmas up and dancing to “I’m Every Woman”. And after Macy Gray took the stage, we moved out into the regular crowd where there was a few thousand people but mostly decent sight-lines.

Gray did some old hits and a lot of stuff from her new album. She talked a lot, in that raspy little girl voice of hers, and kept trying to get hte crowd to be louder. Someone had told her there were 30,000 of us (more like 3,000) and she kept saying “ya’ll are really quiet for 30,000 people!” She did some covers and mash-up things (Radiohead, Dee-Light, Bob Marley and Rod Stewart) and ended the evening by leading a sing-along version of her hit “I Try”.

We were sad at missing Cyndi Lauper (again) but the ladies at Yonge Dundas Square made up for it.

I’m gonna give up trying to ever see Cyndi Lauper I think. I’m convinced that it wasn’t meant to be, and that my memories of Lauper should be the sweet nostalgic ones of the early 80s where she turned the world on its head and encouraged young girls to be “unusual”. I’m still pretty unusual, so  that lesson is enough to take away.