This chapter considers Doris Day and Marilyn Monroe, two of the most popular female stars of the 1950s. Both stars frequently played musical performers in their films, especially Day, who of course had a major career as a recording artist apart from her films. The work of these two actresses foregrounds the issues of gender that were so contested in the 1950s, sometimes confirming, sometimes playing with, and sometimes pushing against American concepts of femininity. These women are often contrasted as ‘girl-next-door’ and ‘sexpot’, but the reality of their films is more complicated, Day not always as demure as subsequent generations have labelled her and Monroe not as transgressive. The music to which and with which they acted confirms and contributes to this complexity.