Since this thread has been revived, I thought I would mention a couple of the interesting uptown fixtures I used to see growing up. There was a guy that would stand at the corner of Bathurst and Wilson who looked a lot like a 1990s-era Michael Jackson. He would stand and wave with a single white glove at every car that passed. The guy disappeared for several years and then resurfaced in the late 2000s only to disappear again. He was kind of like a less threatening Zanta (if you don't know who Zanta is then just don't even bother wasting your time on google).
The other character was the notorious Yonge and Eglinton "Eyebrow Lady". I am sure anyone who has ever seen her will need no further description, but for those that don't, she is/was an elderly woman who could often be found wandering Eglinton East between Yonge and Redpath. She had massive painted on eyebrows that probably stretched upwards of 1.5 inches towards her hairline, and she could always be seen smoking 100 length cigarettes through a classic style holder. I never had any exchanges with her, but there were always unverified "friend of a friend" stories about her that were probably nothing more than just high school gossip from the halls of Northern Secondary.
It was always evident that both of these individuals had mental health issues, and hopefully someone stepped in and got them some help because I haven't seen either one in years.