Oldtimers was born from the convergence of three distinct ideas that unexpectedly came together. Daryl Della’s inspiration began with his grandfather, Henry T. Della, who had previously appeared in Revenge of the Golden Hoot. The initial vision was simple but evocative: a slow-motion shot of Henry walking down Holly Avenue, flanked by neighbor Jack Lewkowitz and Daryl’s Uncle Bill. Around the same time, Ray Revello and Alan Wigley were developing a story imagined for Sean Connery about a group of seniors defending their neighborhood from gang warfare, while Chris Cairo pitched a drama inspired by news reports of elderly individuals selling prescription drugs to make ends meet. These three threads were woven into a single narrative, with the slow-motion sequence as its foundation.

Changes to the cast were inevitable. Uncle Bill was replaced by Ed Kayser due to family tensions with Bill. With Ed taking his place, the story evolved further when Daryl’s father, Hank Della, was brought on to refine the script. Hank reworked the story to add warmth and balance, softening some of the more cynical edges and crafting sharp, memorable dialogue. However, Daryl insisted on keeping darker, riskier elements, most notably the shocking decision to kill off Ed. This move subverted audience expectations by eliminating the film’s comic relief character and delivering an emotional gut punch by killing someone who was playing a version of themself. It was a bold choice that added layers to the film’s exploration of mortality and legacy.