Retro airline ads usually feature either a stewardess, a plane flying overhead, or a beautiful destination where the plane will land. But what about Winston Churchill? For Virgin Airlines, it was the perfect visual fit. They took one of the most admired leaders in British history, and associated the brand with all of his admired qualities. A risk for sure. But Sir Richard Branson, famous founder of Virgin, has never shied away from risk. And the result was likely one of the most intriguing airline ads of the 80s.

FUN FACT: Richard Branson isn’t successful by accident. Apparently his mother had ambitions for him to become Prime Minister of England even before he was born. While he didn’t become the next Churchill, we can say with certainty that he didn’t let his family down. (Source: Business Insider)