Life satisfaction has often been related to one’s personality, but past findings have demonstrated inconsistent relationships between cultures. We posit that cultural values exert a contextual effect on the relationship between personality and life satisfaction. We used data collated from the World Values Survey (N = 33942) as it captured both country- and individual-level information for cultural values, personality and perceived life satisfaction. Cultural values were measured using traditional-rationalism (TR) and survival-self-expression (SS, Inglehart & Baker, 2000. We employed multilevel modelling to observe the contextual effect of culture, via the cross-level interaction for each of the two cultural values at the country level (TR and SS) and each of the five personality traits at the individual level (OCEAN), in predicting life satisfaction. The analyses revealed two significant contextual effects between TR and extraversion (b = 0.06, p = 0.02), and SS and neuroticism (b = 0.09, p = 0.003) in predicting life satisfaction. Further floodlight analyses identified significant regions of influence: Extraversion positively predicts life satisfaction when TR was high. Neuroticism also negatively predicts life satisfaction the more the culture values survival (increasingly negative from normal to low SS). Additional implications for our findings will also be discussed.