https://en.wikipedia.org/wiki/Manulife_Centre , https://manulifecentre.com
https://www.google.com/maps/place/Manulife+Centre
https://www.skyscrapercenter.com/toronto/44-charles-street-west/2979 166 m / 545 ft
Fortunately, 44 Charles wasn't just 44 stories. Indeed, it was the first 51 story mixed-use residential & office complex in Canada, but it should have been taller. Chicago has had the 100 story John Hancock Center since 1969. If Toronto couldn't have its own 100 story building in the mid 1970s, similar in scale to the John_Hancock_Center, there should have been two buildings with more than 50 floos.
https://www.cushmanwakefield.com/en/canada/properties/for-lease/office/on/toronto/55-bloor-street-west/s119707755-l This should have been the first 55 story office tower outside of downtown Toronto.
https://www.loopnet.ca/Listing/55-Bloor-St-W-Toronto-ON/17793768
https://urbantoronto.ca/database/projects/manulife-centre-podium-and-streetscape-renewal.19539
This is a nice, wide Toronto building, but it got Vancouverized or miniaturized, right from the start.
https://www.cbre.ca/properties/retail/details/CA-Plus-268572/manulife-centre-55-bloor-street-w-toronto-ontario-m4w-1a5 It would have been quite impressive if it opened as a 55 story tower.
https://sgconstructors.ca/wp-content/uploads/2021/08/55-Bloor-Manulife-Redevelopment-Profile.pdf
https://urbantoronto.ca/news/2018/09/glazing-enclosing-manulife-centre-addition-bay-and-bloor.33926
Australia was able to go above 99 floors before Canada.
https://en.wikipedia.org/wiki/Australia_108 Actually has 100 floors.
https://en.wikipedia.org/wiki/STH_BNK_by_Beulah 102 floors.
https://en.wikipedia.org/wiki/List_of_tallest_buildings_in_Canada#Under_construction