Growing up in midwestern America in the 1970s and 1980s, the prototypical blonde statuesque Barbie and a myriad of ultra-butch Ken fantasy options were plentiful inspiration to capture a closeted gay boy’s imagination. Utilizing an autoethnographic method, this chapter details the experiences of a queer cisgender filmmaker who uses his childhood connection to Barbie and Ken dolls to fuel the media he creates, and explores the larger cultural relevance of a queer cultural identity. It details the inspiration and production of an internationally screened coming-of-age narrative short film crafted around a Sport & Shave Ken doll. Additionally, it examines the making of a documentary where college students of different races, genders, and abilities remake thrift store Barbie dolls. And, finally, discusses the adaptation of the researcher’s current work-in-progress film project that attempts to tell a gay man’s biography with different generations of Ken dolls. Through connecting the relevance of Ken and the larger Barbie Universe to his art, the filmmaker will reflect on his continuing fascination with the dolls, while also navigating his changing relationship to how it weaves its ways through his own queer storytelling and the impact on producing media for a broader audience.