Legislation is typically passed to accomplish some goal that benefits the majority of society. Sometimes, however, legislation leads to unanticipated and undesirable outcomes. This dissertation examines the ‘side-effects’ of three different Canadian labour laws. Chapter one examines the impact of voting laws on certification success in British Columbia from 1978 to 1998. During that time period, a voting system was introduced in 1984, and was then repealed in 1993. Chapter two examines the impact of welfare cheques on the likelihood of injection drug users leaving the hospital against medical advice (“AMA”), thereby interrupting treatment. The effect of such behavior on subsequent readmission and the probability of an overdose are also estimated. The final chapter utilizes a natural experiment to evaluate the long-run impact of unemployment insurance. The similar UI systems in Maine and New Brunswick in the 1940s and early 1950s were compared over time taking into account the increased generosity of the Canadian system after 1960. Using the five decennial censuses from 1940–1991, the comparison between these two jurisdictions over time is exploited to estimate the effects of UI program parameters on labor market outcomes.