Gilmore Girls Almost Featured Jess In His Own Spin-Off

"Gilmore Girls" is the gift that should have kept on giving. The turn of the century introduced the world to Amy Sherman-Palladino's quippy and banter-heavy series, with audiences tuning in by the millions (via Entertainment Weekly) during its debut season, making it a runaway success for The WB (now The CW). The momentum on the quaint mother-daughter dramedy continued for seven seasons, when the brass behind Stars Hollow decided to call it curtains on the Gilmore family's exploits.

Since wrapping up in 2007, "Gilmore Girls" has emerged as essential television, with outlets like Buzzfeed labeling it as one of the best TV shows ever made. Sherman-Palladino's slice-of-life now boasts more fans than ever, with new converts from all walks of life joining in on the Gilmore fun. The National Post says that the cult-like following "Gilmore Girls" has received transcends "generations, gender and genre," labeling its narrative efforts as timeless. As a cultural phenomenon, it's easy to wonder why The CW doesn't think of "Gilmore Girls" as a never-ending repository from which new stories can be mined from.

Despite the revival series "A Year in the Life" dominating Netflix's charts in 2016 (via CinemaBlend), the future of "Gilmore Girls" remains uncertain. Head to the show's many fan groups online and you'll find several instances of viewers craving any sort of "Gilmore Girls" spin-off or continuation. Before the revival series hit streaming, Sherman-Palladino and the network were developing a spin-off based on Milo Ventimiglia's Jess. Had things gone as planned, Stars Hollow's most ardent viewers would have received fascinating insight into the "Gilmore" world outside of the quaint little town.

With a rich backstory and pliable arc, Milo Ventimiglia's Jess was the perfect "Gilmore Girls" character for a spin-off. The resident bad boy of Stars Hollow quickly became one of the most interesting characters on the series, challenging Rory's (Alexis Bledel) worldview when he showed up in Season 2. The lead-up to what could have been his own spin-off was fascinating, with Amy Sherman-Palladino weaving together an interesting, fish-out-of-water set-up. It all kicked off with Jess uprooting his life to California, attempting to find his estranged father, Jimmy (Rob Estes).

Season 3, Episode 21, titled "Here Comes The Sun" put the focus on Jess in the brand new state, trying to deal with Jimmy. Beyond serving as an intimate and deep dive into the strained father-son relationship, juxtaposing Rory and Lorelai's (Lauren Graham) dynamic, the 2003 episode served as a backdoor pilot for a spin-off wholly dedicated to Jess. Titled "Windward Circle," the series would have focused on Ventimiglia's character finding his footing in sunny California, per Bustle.

Reports from 2003 (via The Futon Critic) reveal that the spin-off had a less than palatable price tag attached to it thanks to the cost of filming on location in California. Planned as a midseason 2004 debut with six episodes, the network ultimately scrapped the spin-off, deciding to pluck the "Gilmore Girls" favorite back into Stars Hollow. Brief footage from the Jess spin-off reveals that the character would have faced significant culture shock, clashing with west coast natives. Ventimiglia ultimately returned as Jess for several guest appearances and was featured in "A Year in the Life."