This paper presents the findings of a qualitative study about the inclusion of arts-based assessment strategies in a 12th grade Israel education classroom. Students were tasked with producing a political cartoon that demonstrated their understandings of contemporary Israeli society. Data was collected from interviews and students' original artwork. The findings revealed that learning through the arts provided students with opportunities to think about and express their feelings about Israel in aesthetically complex and personal ways. The findings also demonstrated the importance of pre-assessment strategies like frequent exposure to the genre of political cartoons and conferencing before submission.