During challenging times art can provide avenues for expressing one’s experiences, developing empathy for each other, and finding a common ground. The last year and half provided educators with unimaginable challenges, but also with some unique opportunities to engage with contemporary issues in the classroom. Nonetheless, many felt ill-equipped to address the difficult topics that have surrounded us in the last few months, including the manifold dimensions of this global pandemic, and the awareness of the gender, health, education, racial, and economic disparities it revealed; as well as an unprecedented economic crisis, coupled with the undeniable effects of climate change. While these issues have collectively impacted us, in many instances instead of promoting unity, we experienced strife and divisiveness. We believe that art educators are uniquely positioned to engage in exploration of the complexities of today’s reality with their students and this article is an invitation not to shy away from difficult topics.