Cigarette ads on television were banned in the UK in 1965note Loose tobacco and cigars, however, were permitted to be advertised until 1991. Cinema ads continued up until 1999, while radio ads were permitted until 2003., and in the US in 1970. Nowadays, they're looked back on as a symbol of how naive people were at the time about the dangers of tobacco use, and as symbols of '50s and '60s kitsch. The knowledge that at least four of the men who played the Marlboro Man in advertisements later died of lung cancer wound up making Marlboro's ads in particular Harsher in Hindsight, especially knowing the lengths to which tobacco companies went to deny or downplay the health risks of smoking.
Erin Esurance was a highly popular mascot for Esurance during the latter half of the 2000s. A pink-haired, Spy Catsuit-clad Action Girl inspired by shows like Alias and Kim Possible, she was a hit among young men and women and greatly boosted Esurance's brand appeal, both intentionally and with unexpected surges of pornographic fan art involving her. In fact, there was so much porn of the character — some of which popped up when people merely searched for Esurance on a search engine — that Esurance had no choice but to ax the character in 2010 and scrub all references to her from their website. Then everyone started questioning why you need some kind of spy, even a sexy one, to sell auto insurance, and all but dismissed her. By The New Tens, she was actually less popular than Microsoft's Clippy, and is understandably Esurance's Old Shame.
In-Universe example: An ad for Pringles potato chips actually mentions this trope. When the kid asking a question about the world's largest disco ball, he gets "Dude, disco is dead." as the answer.