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The Book of Gossage
I really do highly recommend this. Howard Gossage was doing interactive and social and purpose-driven advertising in the 1960s and 70s with print. It’s all very relevant today.
There’s also a good biography on him called “Saving the word is the only job fit for a grown man”
Where the Suckers Moon, about the short, disastrous relationship between Subaru and Wieden in the early '90s, is the most entertaining book about working in advertising that you will ever read.
This is true!
The Anatomy of Humbug is a good primer on how our understanding of how advertising works has changed over time.
Fart: The Musings of an Advertising Gasbag
is an absolute must-read for newbies. Literally taught me everything I know.
I’d say start with Ogilvy on Advertising.
I'll add this to my list! Thank you so much.
I also really like Copywriter: a life of writing ads and other mistakes by Ray Welch. It’s not helpful but very entertaining and a great look into the culture of Boston advertising in the 80s and 90s