Political orientation influences support for free speech, with liberals often reporting greater support for free speech than conservatives. We hypothesized that this effect should be moderated by cultural context: individualist cultures value individual self-expression and self-determination, and collectivist cultures value group harmony and conformity. These different foci should differently influence liberals and conservatives’ support for free speech within these cultures. Two studies evaluated the joint influence of political orientation and cultural context on support for free speech. Study 1, using a multilevel analysis of data from 37 U.S. states (n = 1,001), showed that conservatives report stronger support for free speech in collectivist states, whereas there were no differences between conservatives and liberals in support for free speech in individualist states. Study 2 (n = 90) confirmed this pattern by priming independent and interdependent self-construals in liberals and conservatives. Results demonstrate the importance of cultural context for free speech. Findings suggest that in the U.S. support for free speech might be embraced for different reasons: conservatives’ support for free speech appears to be motivated by a focus on collectively held values favoring free speech, while liberals’ support for free speech might be motivated by a focus on individualist self-expression.