Broken Girl Media

Sara Jean Underwood

Ah, Sara Jean… the last Playmate of the Year that mattered.

By 2007, Hef was distracted with The Girls Next Door and a New Media landscape that he was ill-equipped to navigate, and shortly thereafter, his dotage began to devour him. The magazine was never the same, and couldn’t find a voice for the future.

So in fairness, I’m not sure if SJU was truly representative of Hef’s taste —she had modest, natural boobs back then, and the man loved him some big, fake titties— but even if he just rubber-stamped his editorial staff’s decision, I’m giving him credit for making the right call at the end of an era.