Sheppard’s Season is a modern bro comedy about friendship, failure, and self-discovery. Set in Atlanta, it follows Eric, Jeremy, and PJ — three flawed but lovable guys trying to evolve past their hang-ups while chasing meaning, romance, and redemption.
Episode 1
Eric is an awkward, anxious guy nursing a crush on his coworker, Melissa. His confident friend Jeremy gives him questionable advice over beers in a local Atlanta bar — but somehow, it works. The two debate fate, fear, and The Alchemist, realizing that maybe everyone’s just trying to find their own treasure — even if it’s love.
Episode 2
Six months into his relationship with Melissa, Eric is convinced she's "the one." But during a date night at a restaurant, the arrival of a charismatic waiter named Zeke exposes cracks in their new love. As flirtation and insecurity simmer at the table, Eric's perfect evening unravels, forcing a confrontation about commitment and doubt that threatens to end their relationship before it truly begins.
Episode 3
After a disastrous date night, Eric is left picking up the pieces. Meanwhile, Jeremy's promising date takes a wild turn when he makes a shocking discovery in the same restaurant, forcing him to choose between his friend and a difficult truth. A familiar face alone at a nearby table reveals a secret, and a flirtatious waiter proves that history has a way of repeating itself. Loyalties are tested in Episode 3 of Sheppard's Season.
Episode 4
As Eric struggles to move on, Jeremy takes drastic measures to cheer him up—involving a life-size cutout of his ex and throwing knives. The plan takes an unexpected turn when a weary pizza deliveryman named Jeremy is invited in, forging a hilarious and heartfelt trio bound by tequila and shared misery. This is a story about bad ideas, good pizza, and the brotherhood found in rock bottom.
Episode 5
Feeling isolated and stuck in his messy trailer, Pizza Jeremy scrolls through crypto dreams and watches his obnoxious neighbors from afar. As the weight of his loneliness grows, a vivid daydream of happier times with Jeremy and Eric pushes him to a breaking point. Will he reach out to his old friends, or will his self-doubt keep him trapped?
Behind the Scenes & Stills
Cast & Crew
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Wes Jespersen -
Jay Wooten -
Joey Duke -
Greer Howard -
Violet Sinclair -
Brody Wellmaker -
Ricky Robles-Cruz
