Chicago TV Shows on Netflix: Binge-Worthy Windy City Picks

The Last Summer is a captivating 2019 comedy that provides a poignant look at the transitional period between high school and college. Set in the vibrant city of Chicago, the movie follows a group of recent graduates as they navigate love, friendship, and newfound independence during their final summer together. Directed by William Bindley, the film boasts a talented ensemble cast, including KJ Apa, Maia Mitchell, Halston Sage, and Jacob Latimore, who bring depth and charm to their characters. The authentic Chicago setting, combined with a diverse and compelling soundtrack, enhances the overall viewing experience. With relatable themes of personal growth and life-changing experiences, and memorable quotes like Griffins Sometimes the best things happen when you least expect them, The Last Summer is a must-watch for anyone who has ever faced the uncertainty and excitement of lifes transitions.

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Ma Raineys Black Bottom is a powerful 2020 drama that vividly brings to life a 1927 Chicago recording session filled with tension and ambition. Based on August Wilsons Pulitzer Prize-winning play, the film, directed by George C. Wolfe with a screenplay by Ruben Santiago-Hudson, delves into themes of racial exploitation and power dynamics in the music industry, superbly portrayed by Viola Davis as the iconic blues singer Ma Rainey. Chadwick Boseman delivers a compelling performance as ambitious trumpeter Levee Green, marking his final and unforgettable film role. The movie is a testament to the African American experience of the 1920s, enriched with authentic blues music and meticulous period details. Produced with close collaboration from the August Wilson Estate, Ma Raineys Black Bottom not only provides sharp social commentary but also showcases stellar performances that have drawn critical acclaim and numerous awards. Dont miss this insightful, culturally rich film.

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Win It All is a compelling comedy film that offers more than just laughs. Directed by Joe Swanberg and starring Jake Johnson, the movie presents a relatable and chaotic journey through the life of Eddie Garrett, a small-time gambler who gets in over his head. The films mumblecore style, characterized by naturalistic dialogue and authentic performances, brings a unique authenticity to the storytelling. Set against the vibrant backdrop of Chicago, viewers are plunged into Eddies high-stakes world as he struggles to recover lost money before a friends release from prison. The well-rounded cast, featuring Joe Lo Truglio, Aislinn Derbez, and Keegan-Michael Key, delivers engaging performances that capture the nuanced challenges of addiction, temptation, and redemption. With improvised dialogue and a soundtrack filled with indie and alternative tunes, Win It All creates a raw and immersive experience. If you appreciate genuine characters and captivating narratives, this film is a must-watch.

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Jeff Garlin: Our Man In Chicago is a must-watch stand-up comedy special on Netflix, offering an hour of non-stop laughter. Filmed at the iconic Park West theater, Garlin delivers a stellar performance rich with observational humor that is both hilarious and relatable. The special is filled with personal anecdotes that provide a deeper connection to Garlins life and career, showcasing his comedic genius. Directed by Jonathon Braun, the production captures Garlins dynamic performance from multiple angles, making viewers feel like they are part of the live audience. Best known for his role in HBOs Curb Your Enthusiasm, Garlins ability to blend storytelling with humor is unparalleled. Whether youre a long-time fan or new to his work, Our Man In Chicago is a delightful experience that will leave you in stitches. Dont miss the chance to enjoy Garlins wit and charm in this engaging and memorable stand-up special.

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Why You Should Watch Uncle Buck Uncle Buck, directed by the legendary John Hughes, is a timeless comedy that blends humor and heart in a way few films manage. With John Candy delivering a standout performance as the lovable yet irresponsible Uncle Buck, the movie takes you through his hilarious and unconventional child-rearing antics. This 1989 classic explores themes of family, responsibility, and love, providing laugh-out-loud moments and touching life lessons. The film's insightful portrayal of familial bonds and personal growth, underscored by a memorable soundtrack, makes it a must-watch. Whether you're looking to revisit the charm of 80s cinema or experience an incredible comedy for the first time, Uncle Buck offers an unforgettable viewing experience filled with joy, laughter, and heartwarming moments. Don't miss out on this quintessential feel-good film that promises to entertain and inspire.

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