Bob Hawke, prime minister of Australia (1983-1991) was a ‘man’s man’, a drinker and womaniser. He was also prone to public displays of weeping which were much debated at the time but appeared to do little harm to his popularity. Recently Frank Bongiorno described Hawke’s teary displays as ‘a notable landmark in the history of Australian masculinity and the evolution of its emotional life’. This paper compares the late-twentieth century weeping of Bob Hawke with the equally plentiful early-twentieth century tears of Winston Churchill and eighteenth century histrionics on the floors of the Houses of Commons and Lords, to interrogate the circumstances in which men’s tears become powerful. It argues that although overt emotion has long been a hallmark of politics, the efficacy of a politician’s moist eye or stifled sob is not only historically contingent but also dependent on the fit between contemporary constructions of masculinities, the type of tears and the circumstances in which they are shed.