The current study examined whether differences in the sense of freedom explain the differences in the levels of well-being between Japanese and American populations across several decades (1981–2011). A series of mediation analyses were conducted on five individual waves of datasets from the World Values Survey. Meta-analyses were also employed to examine the summary indirect and total effects across waves from the country dummy variable to life satisfaction judgments via the sense of freedom. The final sample consisted of 5534 Japanese and 6176 American respondents across all study periods. The main findings were that (a) indirect effects via the sense of freedom largely contributed to the difference in life satisfaction judgments between Japan and the United States on all waves, and (b) summary effect sizes across waves estimated by meta-analyses also supported these findings, although the results showed some systematic between-wave variability in indirect and total effects. In conclusion, Japanese people exhibited lower levels of well-being across time, mainly due to their lower levels of sense of freedom compared with American people.