All 12 Craig Cackowski Movies In Order — All The Best (And Worst) Films To Watch Online

Rodolfo Bailey
6 min readMay 22, 2024

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If you’re a fan of quirky comedy, you’ll want to sit back, relax and prepare for an exploration of Craig Cackowski’s films. Known for his unique humor and eccentric characters, we’ll dive into the world of Craig Cackowski and take a closer look at his movie career. From hilarious performances to thought-provoking storylines, this roundup will give you a glimpse into what makes Craig Cackowski’s movies stand out from the rest.

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1. Moonpie (2006)

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In the heartwarming indie dramedy “Moonpie, “ two seemingly mismatched individuals find solace in their tumultuous lives. Drowning in work and personal struggles, an exhausted elementary school principal crosses paths with a quirky third-grade teacher who battles her own battles with bipolar disorder. As their worlds collide and their relationship develops, the two begin to discover a sense of normalcy and happiness that seems almost too good to be true.

👉 Watch for free with Prime

2. Year of the Dog (2007)

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“Dog Year” is a heartfelt tale of a secretary, portrayed by Molly Shannon, who experiences a surprising twist in her life following the unexpected loss of her cherished Maltese dog. The movie delves into the profound bond that develops between the main character and her newfound canine companion, a captivating mixed-breed who unexpectedly comes into her life.

🎬 Watch now for free @ Amazon Prime

3. 21 & Over (2013)

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“21 & Over” is a hilarious and heartwarming comedy film that follows the journey of a young, dedicated college student on the night before his big medical school interview. Along with his two best friends, they celebrate his 21st birthday in true college fashion. As the night unfolds, the trio finds themselves in a series of unexpected and outrageous situations that test their friendship and push them to their limits.

📺 Watch free from Amazon Prime

4. The Kings of Summer (2013)

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In a heartwarming coming-of-age tale, “The Kings of Summer” follows the journey of three teenage friends as they embark on the ultimate adventure — building a house in the woods and experiencing the joys and challenges of living off the land. Unraveling a tale of friendship, love, and the power of youth, this indie-drama offers viewers a whimsical and touching look at the trials and tribulations of adolescence, as the boys navigate their way through a summer filled with laughter, romance, and a love triangle that will test their bonds. Director Jordan Vogt-Roberts and writer Chris Galletta have crafted a delightful and unique story that explores the complexities of teenage relationships, all set against the backdrop of one unforgettable summer.

📺 View free @ Prime

5. Thrilling Adventure Hour Live (2015)

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Join the lively and captivating world of Thrilling Adventure Hour Live, where music meets storytelling like never before! This incredible concert film features the beloved live show and podcast, bringing together laughter, adventure, and unforgettable performances.

📽️ Stream for free @ Amazon Prime

6. Glitch (2015)

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“Glitch” (2015) is a heartfelt indie comedy-drama starring Lucas Neff, Maiara Walsh, and Blake Silver. Set against the backdrop of the tech industry, the film follows an ambitious app developer, who finds himself entangled in a complex love triangle with the girl he’s fallen for.

➡️ View free at Amazon Prime

7. Seven Stages to Achieve Eternal Bliss (2018)

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Experience dark comedy, thrills, and chills in the unconventional, yet captivating film ‘Seven Stages to Achieve Eternal Bliss’ (2018), directed by Vivieno Caldinelli. This movie, starring Taika Waititi, Rhea Seehorn, and Kate Micucci, centers around a small-town couple searching for their big city dreams when they stumble upon the perfect apartment. However, they soon discover the apartment’s dark past — the site of a deranged cult’s ritualistic suicides.

📽️ Stream for free from Amazon Prime

8. Paul F. Tompkins in conversation (An SF Sketchfest Tribute) (2018)

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In January 2018, SF Sketchfest proudly honored the talents of comedian, writer, and actor Paul F. Tompkins with a heartfelt tribute.

👉 Stream now for free at Amazon Prime

9. Wine Country (2019)

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Wine Country, a 2019 comedy film directed by Amy Poehler, follows a group of long-time friends as they reunite in Napa Valley for a hilarious and heartfelt adventure. The laughter-filled reunion sparks discussions about their past choices, bringing them closer together. With a stellar ensemble including Poehler, Rachel Dratch, and Ana Gasteyer, this film offers a fresh take on friendship and nostalgia.

📺 Stream for free with Amazon Prime

10. For Madmen Only: The Stories of Del Close (2020)

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For Madmen Only: The Stories of Del Close is a riveting documentary film that explores the life and impact of legendary improv guru Del Close. Del Close was a visionary and eccentric performer who helped shape the world of improvisational comedy. This powerful documentary delves into Close’s unique and unforgettable journey, providing an intimate look at his life, work, and lasting influence on the entertainment world.

📽️ Stream free @ Prime

11. Murder Bury Win (2020)

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In “Murder Bury Win, “ three friends, Jake, Paul, and Chris, devise a card game called “Murder Bury Win” with dreams of fame and fortune. With no success in funding their project, an enigmatic stranger offers to publish their game if they surrender ownership and credits. When a dispute over the gaming rights ensues, they decide to fight back.

📺 Watch free at Amazon Prime

12. Magazine Dreams (2023)

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In the 2023 release, “Magazine Dreams, “ a Black amateur bodybuilder navigates the complex world of celebrity and violence while searching for genuine human connections. This gripping drama explores the dark side of fame and the consequences of exploitation.

➡️ View now free at Prime

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