Cross-gender performance in Indonesia has been examined largely as stage practice, and face painting largely as a technical adjunct to costume and choreography; neither body of work accounts for what happens when the painted face becomes the principal carrier of meaning in a piece made for circulation on a social media platform. This article examines the visual form, the symbolic meaning, and the self-expression articulated through face painting in the Lathi Challenge uploaded to the YouTube channel of Didik Nini Thowok, the dancer recorded by the Indonesian World Record Museum as the first cross-gender dance artist in the country. The study is qualitative and situated within cultural studies, drawing together the aesthetic theory of The Liang Gie, sign categories as applied to performance by Sahid, Butler’s account of performativity, and McNeal’s theory of drag performance. The corpus comprises the four painted faces that structure the video, analysed alongside non-participant observation of the artist’s digital activity between October 2024 and October 2025 and semi-structured interviews with makeup artists, dancers, and practitioners of Javanese character makeup; the material was triangulated by source and by technique and analysed through the interactive model of Miles and Huberman. The analysis finds that the four faces move from a complete Javanese feminine face towards a bilaterally symmetrical death’s head; that the decisive face is the second, on which the two registers are held at once and divided horizontally across the middle; and that red migrates from the cheek and the lip to the gum line, turning cosmetic colour into exposed tissue. Face painting thus operates as a medium through which gendered identity is negotiated for a scrolling audience.