An eccentric theater artist struggles to stage an OJ Simpson musical with the help of his childhood friends.

Jess, age 18, and Moss, age 12 are second cousins in the dark-fire tobacco fields of rural Western Kentucky. Without immediate families that they can relate to, and lacking friends their own age, they only have each other. Over the course of a summer they venture on a journey exploring deep secrets and hopes of a future while being confronted with fears of isolation, abandonment and an unknown tomorrow.

The Most Fun I've Ever Had With My Pants On follows two childhood girlfriends Andy and Liv who reunite to scatter Andy's dad's ashes from LA to Austin where Liv will audition for the role of a vixen spy in a noir film. Between performing mini-funerals in surreal southwestern landscapes, the girls practice being bad. Hilarious dialog, military cross-dressing, an incredible underground soundtrack, and performances by Sarah Hagan (Freaks and Geeks, Buffy the Vampire Slayer) and writer/director Drew Denny in this mixed media dark comedy that interweaves autobiography, documentary, fiction and camp.