Regina Spektor reflects on her immigrant journey from Moscow to the Bronx, initially aspiring to be a classical pianist but eventually evolving into a singer-songwriter. She explains how a trip to Israel and improvising songs for fellow travelers sparked her transition from classical music to songwriting. Regina discusses the influence of her Jewish heritage on her music and her performance style, which often incorporates different perspectives and literary influences. During the interview, she performs live songs, including Leonard Cohen’s "Chelsea Hotel #2", a preview of her performance of three cover songs for the Jewish Music and Heritage Festival.