I looked at various selections of 'best songs of Joe Dassin' on YouTube and it's interesting to see how they differ (see below). As for me, here are the five songs I prefer (extracted from those lists)
Guantanamera (1966) - 20:54, Siffler sur la colline (1968) - 12:39, Les Champs-Élysées (1969) - 01:25:38 , L'Amérique (1970) - 30:06, L'Été indien (1975) - 01:13:05
Wikipedia sort of agrees:
By the early 1970s, Dassin's songs were on the top of the charts in France and he had become immensely popular in that country. He recorded songs in German, Spanish, Italian and Greek, as well as French and English. Among his most popular songs are "Les Champs-Élysées" (Originally "Waterloo Road") (1969), "Salut les amoureux" (originally "City of New Orleans") (1973), "L'Été indien" (1975), and "Et si tu n'existais pas" (1975).
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