Speakout 7-11. You can buy a SIM card, airtime voucher, and even a phone with cash at any 7-11 store. No need for your name or any other personal info and no contract. Runs on the Rogers network so coverage/reception is good. You register the SIM online but you don't need to make an account or anything, and even if you make one you can use any name and email. Airtime voucher can be loaded by dialing a USSD code. Same for checking your balance.
They have a promo now where if you buy $100 airtime you get an extra $25, free SIM, and $30 off a phone (reg $80). So for $150 + tax you can get $125 airtime + SIM + cheap Android phone. I think airtime is $0.30/min and outgoing texts are $0.15 each, but they also have monthly plans. I spend around $10/month which is worth it for the privacy and convenience IMO.