A long, long time ago I used to have a retail bookstore. At that time smaller publishers couldn't justify the expense of a salesman so they paid some goober to call and read whatever promotion they had going on. In describing one of the promotions he said, "this book is written for teenagers by a man who is an ex-teenager himself."
I pointed out that it's kinda hard to skip those years and go straight to adulthood - he acted offended. I'm guessing the ad writers decided to have fun with this socially challenged individual.
Every spring, the local farm-and-feed store has a prominently displayed sign saying
Pick Up Chicks Here.
It's really true. They're in an incubator next to the cash register.
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On the Not So Successful side was the local connectivity company's TV ad that began with an establishing shot of an isolated cabin in the woods. You were supposed to see the cabin and think "19th-century settlers who need to move into the present century by using our service". Unfortunately I didn't; I thought "satellite internet"-- a service the company doesn't provide, and if they did, it would be lousy. Some appropriately targeted market research would have nipped that particular ad in the bud.
There is a pet food firm that had a slogan. "Nothing is better for your pet." You can feed our stuff, or nothing. Nothing is better. It's not on the web anymore, but I still see it on their trucks on the highway.
Best one I ever heard was one a mate told me about how he used to drive to work past this building site with an obviously asian firm working there as the banner said: 'you've tried the cowboys, now try the indians.' Classic.