Though HBO is widely considered the premiere prestige television network (lookin' at you, Westworld and Game of Thrones), and we all know how successful Mad Men turned out to be (hello, multiple Golden Globe Awards), the company's executives passed on an opportunity to air the show. Or, more specifically, HBO paragon and Sopranos creator David Chase did.
We know what you're thinking: it's odd that the network known for dark, gritty, and overtly adult content would reject a series full of that stuff. Matthew Weiner thought so, too. According to Chase, HBO expressed initial interest in the series, and appeared to indicate they'd back the show as long as Chase served as executive producer. Chase and Weiner reportedly tried to negotiate a mutually beneficial agreement, but things fell through. While Chase was "very tempted" by the idea of executive producing Mad Men and even directing the pilot episode, he declined and walked away, citing his desire to "move away from weekly television." To this day, it's unclear exactly why HBO passed, as the network never gave Weiner a full explanation—a lack of closure he appears to still struggle with. "I would go through David Chase's garbage if I was at HBO, trying to find more of what he does," he admitted. "But they were not like that."
However rocky the show's early road might have been, the ending was sweet: AMC saw Mad Men's promise and picked it up as its first original series. As president Ed Carroll later stated, the network "took a bet that quality would win out over formulaic mass appeal [and] there's no doubt it paid off."