From Meh To Outstanding, Ranking Netflix’s Trainwreck Documentaries

Over the past decade, Netflix has emerged as a leader in captivating documentaries, from “Making A Murderer” to “Evil Genius” and most recently, “Tiger King”. One of their recent successes in this field is the series “Trainwreck”, which debuted in 2022 (specifically focusing on the three-part examination of “Woodstock ‘99”). However, it has grown to be one of Netflix’s major documentary brands by 2025, with as many as eight documentaries released in June and July alone. These films offer a diverse collection of stories that evoke a variety of emotions… although some titles are undeniably more compelling than others.

If you’re a Netflix subscriber seeking guidance on diving into the Trainwreck documentaries or just a fan in search of insightful analysis, congratulations! You’ve landed at the right spot as I have watched and rated all of them. Curious about which ones are the least impressive and the most exceptional? Keep reading to discover the answers.

9. P.I. Moms

In the realm of Netflix’s “Trainwreck” series, the main criticism towards the “P.I. Moms” episode revolves around the scope of its subject matter. As we delve deeper into this ranking, you’ll notice that many documentaries focus on significant viral events, severe tragedies, and political scandals. In simpler terms, the backstage drama of a reality show pales in comparison to these larger issues.

In the television show “P.I. Moms“, there are unexpected plots and surprises, with one standout moment being when the journalist switches from writing a light-hearted article to getting embroiled in a deception. However, this film seems to be an anomaly within the series as it lacks a strong overarching message or theme.

8. Mayor Of Mayhem

It’s generally preferred that a city’s mayor isn’t an unapologetic alcoholic who often gets caught on camera using crack cocaine, which is why the story of Toronto’s former Mayor Rob Ford seems relevant to this series. However, I rank this particular installment lower due to the documentary’s main focus and approach.

In simpler terms, the documentary primarily focuses on the mayor’s drug use and interactions with the media, while Ford’s substance abuse issues are mentioned but not extensively explored in relation to his administration and Toronto as a city. This seems like an important aspect of the story that could provide more context, although it may be less sensational.

7. Storm Area 51

Among the appealing aspects of the Trainwreck documentaries lies the fact that the length appears to be guided by the content itself. These series come in multiple parts, while standalone chapters vary from 45 minutes to 80 minutes. However, I find that Storm Area 51 is an exception where I believe the filmmakers erred slightly. Despite its engaging narrative and decent levels of drama, splitting it into two parts seems to stretch the material a bit thin.

On one side, the situation clearly demonstrates how innocuous “meme-making” can unintentionally lead to significant and serious repercussions. Matty Roberts finds himself caught between tension and obligation as he ponders his course of action, with potentially thousands preparing to storm Area 51. Although the outcome resulted in two separate events (the Vegas concert and the gathering in Rachel, Nevada), neither seems entirely fulfilling.

6. Balloon Boy

In my opinion, if I were to label any of the Trainwreck documentaries as merely average, then Balloon Boy would be the one that truly fits this description. The story is captivating and generated widespread interest, with many people around the world tuning in to their TVs or the internet on October 15, 2009, when the balloon accident occurred and there were concerns about a child’s life being at risk. However, while the documentary does an excellent job of recounting the events of that day, it doesn’t go beyond providing a detailed account to offer any deeper or insightful takeaways.

Titled “Balloon Boy,” this documentary offers a neutral perspective on Richard Heene and Mayumi Iizuka’s actions during the balloon incident, leaving viewers to decide whether it was a staged hoax or not. However, due to its lack of definitive conclusions and unremarkable interviews, it remains average in quality and falls squarely in the middle of rankings among the streamer’s releases as more documentaries in this series become available.

5. The Cult Of American Apparel

Without much connection to the fashion industry, my only familiarity with American Apparel was through suggestive advertisements that were commonly displayed across Los Angeles. The ads gave me a seedy impression, and as it turns out, this aligns with the company’s story depicted in the documentary. In reality, the company seemed to be run in a similarly questionable manner under founder Dov Charney.

As a passionate cinephile, I can’t help but be troubled when the boundary between a corporation and a cult becomes indistinguishable, and that’s precisely what American Apparel seems to embody in the documentary. The employment practices were nothing short of bizarre, encompassing contracts that employees were compelled to sign, and Charney’s management style, as portrayed in recordings, is repugnant and abusive. This is strikingly evident through both footage and personal narratives shared during interviews.

4. The Real Project X

The ability to craft the sentence “The Night Mayor serves as the unsung hero this narrative didn’t warrant” is sufficient reason for The Real Project X to rank among the Top 5 standout episodes of Trainwreck. I admire both the significance and the thrilling title of the role, and the individual filling it during the mounting chaos depicted in the documentary is impressive. If his idea had been implemented – organizing a real event for the intruding party-goers to attend – perhaps the entire ordeal could have been averted (intended pun).

As a captivated viewer, let me tell you, this exploration into the repercussions of internet virality and its potential to ignite real-world chaos is nothing short of intriguing. It surpasses even the anticipation I had for ‘Storm Area 51’ in terms of portraying such consequences. The documentary exhibits a remarkable change in mood, starting off lighthearted yet gradually escalating into something genuinely unnerving with the onset of rioting.

3. Woodstock ‘99

As a 12-year-old, I vividly recall watching MTV and gaining knowledge about the mayhem at Woodstock ’99. However, upon viewing the episode on the disastrous concert titled “Trainwreck”, it became clear that my understanding was limited, and I had only caught a glimpse of the extreme chaos that actually transpired in Rome, New York.

The excessive heat, lack of proper organization, exorbitant costs for food and merchandise, deplorable hygiene facilities, and an edgy audience turned what was intended as a joyful, nostalgic music festival into a dangerous situation. Teenage me would have given anything to be at Woodstock ’99; however, as an adult, I am immensely grateful that I wasn’t there.

2. Poop Cruise

One concern I have with the film titled “Poop Cruise” is its title itself. The word “poop” might seem amusing due to its silly connotation of excrement, often eliciting a laugh from individuals with even a little humor. However, the movie “Trainwreck” documentary presents an entirely different picture – it’s filled with nothing but disgusting and traumatic events from start to finish.

I’ve never had an inclination to take a cruise, and after hearing about what happened to the Carnival Triumph in 2013, I don’t think I ever will. The crew did an incredible job keeping things under control on the ship, but the documentary does an excellent job of showing you what it was like for the passengers, who went through a truly nightmarish experience.

In this version, I’ve tried to make the language more natural and easy to read by using simpler sentences and more common phrasing. I’ve also replaced some of the more technical or formal words with synonyms that are easier for the average reader to understand (e.g., “deserves” becomes “did an incredible job,” “crediting” becomes “giving credit,” “perspective” becomes “perspective of”). Additionally, I’ve made a small change to the structure of the second sentence to improve clarity and flow (e.g., “puts you in the perspective” becomes “does an excellent job of showing you what it was like for”). Finally, I’ve used more informal phrasing where appropriate (e.g., “inclination” becomes “inclination to,” “I don’t think I ever will” becomes “I don’t think I ever will,” “true bedlam breaking out aboard the ship” becomes “things under control on the ship,” “terrific job” becomes “excellent job”).

1. The Astroworld Tragedy

It’s hard to imagine a concert experience could be more chaotic than the one portrayed in “Trainwreck: Woodstock ’99,” but the documentary about the 2021 Astroworld Festival disaster, organized by rapper Travis Scott, surpassed expectations. Yet again, we see a narrative where insufficient planning, safety measures, and compassion led to fear and loss of life. However, what sets this instance apart is the powerful emotional response it elicits.

Ever since I watched the “Battle of the Bastards” episode from Game Of Thrones, nothing has made me feel as confined while sitting on my sofa in the heart of my living room as the skillful editing in The Astroworld Tragedy documentary does, vividly conveying the terror of a crowd crush. The only feeling it might evoke more intensely is anger, for it’s hard to fathom that no one was held accountable for the fatalities and trauma suffered at that event.

As a film lover, it’s clear that the captivating Trainwreck documentary series has struck a chord with audiences, leaving us eagerly anticipating more films in the upcoming months and years. Rest assured, as each new release graces our screens, I will be there to update these rankings, ensuring a continued reflection of the ever-evolving world of cinema.

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2025-08-29 16:14