To cultivate imagination and empathy among school students is a basic challenge for history teachers. This paper examines the relative roles of the teacher and student in nurturing imagination and empathy in the Singapore history classroom, specifically, through source-based studies. Both imagination and empathy are ways for students to think critically about history and, more generally, to develop a passion for learning. This paper demonstrates how curriculum can help Secondary Two history students reenact the past in their own minds and achieve historical empathy, using a range of sources on housing in Singapore in the 1950s and 1960s. (Contains 40 notes.)