Todd Haynes’ 1988 film Superstar: The Karen Carpenter Story used Barbie dolls to reenact the life of the singer and the anorexia nervosa that led to her tragic death. Beyond the obvious correlation between skinny dolls and an emaciated star, Haynes cast his ‘actors’ in order to explore character identification and societal pressures. The film’s success at festivals and later online cult status are a testament to the validity of Haynes’ aesthetic choices. This chapter examines Superstar as a reflection of our deep-seated attraction to objectification and nostalgia. Using social analysis, it compares Barbie’s’70 s identity, exemplified by the launch of Malibu Barbie, with the rise and scrutinization of Karen Carpenter. Film analysis shows the innovative multimedia manner in which Haynes builds a biopic around toys that come with their own emotional baggage. Superstar’s legacy is also considered, inspiring other filmmakers and cut-price comedians to tell their own stories with Barbie in the lens. With a cynical eye and a flair for the melodramatic, Haynes compares Carpenter’s obsessive need to mold her looks and destiny with our own desire to control our childhood toys and our pop culture heroes.