Our objective is to describe associations between media usage and multiple wellbeing indicators in a nationally representative sample of Canadian youth (CSTADS 2012–13) enrolled in grades 7 to 12 (N = 41,057). Youth reported media usage (television/movie viewing, videogame playing, and surfing the internet), wellbeing (academic achievement, school connectedness, self-esteem, physical activity, intake of fruits and vegetables, and bullying), and psychological (drug use, drinking, and smoking) and sociodemographic confounds (ethnicity, grade, province, gender). Videogame playing was negatively associated with academic achievement, b = −0.07 (99% CI, −0.08–05), physical activity, b = −3.09, (99% CI, −3.63–2.56), school connectedness, b = −0.03 (99% CI, −0.04–0.02), self-esteem, b = −0.13 (99% CI, −0.16–0.09), and the consumption of fruits and vegetables b = −0.07 (99% CI, −0.11–0.03). Internet usage was negatively related to self-esteem, b = −0.25 (99% CI, −0.28–0.21), school connectedness, b = −0.03 (99% CI, −0.03–0.02), academic achievement, b = −0.02 (99% CI, −0.03–0.002) and physical activity b = −1.42 (99% CI, −1.92–0.91). Finally, television exposure was linked with less fruits and vegetable consumption, b = −0.09 (99% CI, −0.12–0.06), academic achievement b = −0.05 (99% CI, −0.07–0.04), school connectedness b = −0.02 (99% CI, −0.03–0.01), self-esteem b = −0.06 (99% CI, −0.11–0.003), and physical activity b = −1.09 (99% CI, −1.64–0.54). Internet, television/movies, and videogame time also increased the odds of bullying others by 9%, OR = 1.09 (99% CI, 1.04–1.14) 8%, OR = 1.08 (99% CI, 1.01–1.16) and 7%, OR = 1.07 (99% CI, 1.01–1.14) respectively. Overall effect sizes were small yet may represent significant impairment for heavy media users. Keywords: Media usage, Academic achievement, School connectedness, Physical activity, Self-esteem, Bullying, Fruits and vegetables, Wellbeing, Youth