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12 movies similar to Windfall — OmList

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12 movies similar to Windfall

similar, not necessarily similarly great. that’s what your rec list is for.

Simpsley

2026

Russell Howard: Recalibrate

Russell Howard: Recalibrate

2017

Bill Burr: Drop Dead Years

Bill Burr: Drop Dead Years

2025

Ricky Gervais: Mortality

Ricky Gervais: Mortality

2025

Driver's Ed

2025

Fun with Dick and Jane

Fun with Dick and Jane

1977

Joy Ride

2023

The Best Man Holiday

The Best Man Holiday

2013

Taking Care of Business

Taking Care of Business

1990

Accident Man

2018

Hard to Die

1990

Wake Up, Ron Burgundy: The Lost Movie

Wake Up, Ron Burgundy: The Lost Movie

2004