It's the least important most important business out there, as Don Draper might put it. Advertising: a field that has awed, inspired, tricked, and smeared, all at once, and to the tune of $150 billion each year. The industry saw its heyday in the 1960s--if you watch AMC's "Mad Men," you know this--with iconic ads such as the Marlboro Man (whose creator was the basis for Don Draper's character) changing marketing messaging for good. Looking back, of course, many of the ads from that era--women caged in the name of martinis, messages to "trust your banker"--don't quite translate to the modern day. With the finale of this season's "Mad Men" approaching, we sifted through the NEWSWEEK archives to choose our favorite, most outrageous, most ridiculous mad ads. --Jessica Bennett
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