A large number of artists with Jewish American backgrounds have been deeply influential to the development of comics (notably of the superhero variety), social and political cartoons, and graphic novels. This chapter examines the recurrence of trauma and grief in the works of several Jewish authors, both as core motifs and as narrative/visual devices. It follows the career of graphic pioneer Will Eisner, who moved from realistically drawn crime and adventure fiction (with The Spirit, an early example of long-form comic appealing to adult readers) to more personal themes such as family history and loss in A Contract with God, the first US publication self-labeled as a “graphic novel.” Art Spiegelman’s work (Maus, 1986 and 1991; In the Shadow of No Towers, 2004) confronts similar themes grounded in trauma, suffering, and transgenerational testimony, where the artist’s memorialization of the past and experience with the present construct a graphic negotiation with grief. The chapter finds echoes of this approach in more recent works from Jewish graphic novelists such as Roz Chast and Ken Krimstein.