This article examines two texts which contain representations of the female hobo: Harold Gray's comic strip Little Orphan Annie (1924–1964) and Marilynne Robinson's novel Housekeeping (1980). This article will focus on a section of Orphan Annie from 1926 and 1927. The many differences between the texts – which include their genre and their temporal setting and production – are acknowledged. However, I am primarily concerned with the figure that unites these disparate texts: the female hobo. This article makes use of two key concepts: the category and the frame. There are several categories within these texts: wife, mother, orphan, daughter, and that of wanderer. This article is also concerned with the collapse of categories. Marjorie Garber argues that the presence of a passing figure reveals a 'category crisis'. In Garber's argument this is 'a failure of definitional distinction, a borderline that becomes permeable, that permits of border crossings from one (apparently distinct) category to another' (1993:16). The texts examined in this paper both contain passing figures: Orphan Annie features Annie as a crossed dressed female hobo and Housekeeping a hobo attempting to become a small town mother.