The longest running series of chess ads was undoubtedly the George Koltanowski solving tourneys sponsored by Paul Masson in the early 1960s. Here's a graphical overview.
Although I've guessed at some of the contest numbers and years, the captions should be substantially correct. I'll flag any errors if I discover them.
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Later: Looks like I missed one. The description of this ad said, 'a great original vintage ad removed from a 1966 New Yorker magazine', placing it sixth in the sequence shown above.
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