1. Roger Sterling’s acid trip
For the first half, Season Five wasn't just the best Mad Men season – it was shaping up to be the greatest run any TV show has ever had. It didn't quite get there – the title is still held by Season Four. But this was the White Album of Mad Men seasons, a risky mess where Don Draper and his crew of hustlers finally meet their match in the madness of 1966. Draper couldn't even make it all the way through his first listen to Revolver. The whole season was a full-on portrait of America in the Sixties: drugs, blow jobs, civil rights, Sally's go-go boots. And if this was Mad Men's White Album, Roger Sterling's LSD trip was the "Dear Prudence." You always knew somebody at Sterling Cooper Draper Pryce was going to get psychedelic, but who the hell thought this guy would be the one to chase the white rabbit? In the summer of 1966, Roger – the last guy you'd ever call cosmic – gets a weird psychedelic glimpse of his future and peeks into the nearest faraway places in his lost soul. He sees everything that's wrong about his life. But then his spiritual bliss wears off and he goes back to being his corrupt, cynical self. That's bad news for him – but good for us, because Mad Men just keeps peaking creatively and is still far ahead of anything else out there on TV.