You can watch "Win It All" on Netflix, as it is a Netflix original film. Released in 2017, the movie stars Jake Johnson as a gambling addict who finds himself in a precarious situation after being entrusted with a duffel bag full of cash. To view it, simply have an active Netflix subscription and search for the title on the platform.

"Win It All" is a 2017 comedy-drama directed by Joe Swanberg and stars Jake Johnson as a compulsive gambler who finds himself in a moral dilemma when he discovers a duffel bag filled with cash. The film has received generally positive reviews for its relatable characters and humor, along with Johnson's performance. It explores themes of addiction, responsibility, and personal growth. While it may not appeal to everyone, fans of indie films and character-driven stories often find it enjoyable and thought-provoking.

As of October 2023, the #1 movie on Netflix of all time is "Red Notice." Released in November 2021, this action-comedy stars Dwayne Johnson, Ryan Reynolds, and Gal Gadot. The film follows an Interpol agent who teams up with a renowned art thief to catch an elusive criminal. "Red Notice" gained massive viewership, becoming the most-watched film on the platform, thanks to its star power and entertaining storyline. However, rankings may change over time, so it's best to check for the latest updates on Netflix.

"Win It All" was filmed in Chicago, Illinois. The movie showcases various locations throughout the city, capturing its urban landscape and atmosphere. Directed by Joe Swanberg, the film features a mix of outdoor and indoor settings that contribute to its storytelling, highlighting both the charm and challenges of the protagonist's life as he navigates gambling and personal relationships.