Workplaces constitute sites where individuals “do gender” while at the same time constructing their professional identities and meeting their organisation’s expectations. In most workplaces, a rather narrow range of masculine styles of interaction are considered normative. Discursive strategies associated with stereotypically masculine speech styles, as well as behaviours associated with the enactment of hegemonic masculinity are generally viewed as paradigmatic ways of interacting at work. Drawing on data recorded in a range of New Zealand professional organizations, this paper investigates a range of ways in which normative masculinity is manifested in participants’ discourse, and how notions of masculinity are explored and exploited in workplace interactions. The investigation focuses on one particularly versatile discursive strategy frequently employed in talk at work, namely humor.