Every ‘Trainwreck’ Documentary Released So Far on Netflix, Ranked

The Trainwreck documentary series on Netflix has taken viewers by storm, showcasing some of the most disgusting, heartbreaking, and bizarre events in recent history. From poopy cruises to terrifying concerts, it’s hard to look away from these documentaries, with a few of them being especially thought-provoking—and horrifying.

In this list, we’ve ranked the Trainwreck series based on how effectively each version shared its story and what we were able to take away from the experience. This includes how immersive each story was, how memorable, and how well they were able to deliver suspenseful, unexpected scenes while maintaining honesty and respect for those most affected.

5

‘Mayor of Mayhem’

Following the infamous Mayor Rob Ford and his various scandals, Trainwreck: Mayor of Mayhem begins during a garbage strike that leaves Toronto residents desperate for change. That change seemingly comes when Ford decides to run for mayor, quickly winning people over with his lack of filter and clever publicity stunts, as well as some genuinely helpful contributions to the community. He wins the election, but soon after, problem after problem appears, from allegations that he’s an alcoholic to videos of him smoking crack. Ford continues to proclaim his innocence, causing many people to doubt the accusations against him even in the face of undeniable proof. In the end, Ford died of cancer, leaving behind a legacy that was as entertaining as it was disturbing and tragic.

Humanizing and Haunting

When asked to define Ford’s legacy, the documentary’s interviewees used a variety of words, from “dishonest” to “selfless” and “unpredictable.” Ultimately, as news reporter Katie Simpson said, “It all comes down to who you ask.” While the documentary does a good job of humanizing Ford, it also honestly portrays his many faults and shortcomings, creating a nuanced, engaging story. Additionally, its message about how desperate people will sometimes follow a charismatic leader, even when he goes against their best interests, is timely and important. However, most of the more interesting or shocking moments are given away early on in the documentary, making the larger narrative and Ford’s eventual fallout somewhat predictable, and less compelling.

4

‘Poop Cruise’

A fun trip to Mexico turns into a disaster movie when the cruise ship Carnival Triumph experiences an engine fire and loses power. Now, the passengers have to contend with lack of cell service, intense heat, and spoiled food, but that’s only the beginning. Things get so much worse when the toilets stop working, and later, start overflowing. Soon, the passengers—including a father and his daughter, a group of women at a Bachelorette party, and a man trying to impress his soon-to-be father-in-law—are in for a journey that is as memorable as it is miserable.

Gross but Great

For all its horrors, Trainwreck: Poop Cruise is a lighter watch than most (if not all) the documentaries on this list. It contains some truly funny interviews and memorable lines. The documentary also explores class disparity, corporate lack of accountability, and how easy it was for people to turn on each other during times of crisis. If you’re looking for a laugh with socio-political commentary, this one’s at the top of our lists, but the overall story isn’t quite as impactful as others in the franchise.

3

‘Woodstock ’99’

Broken into three episodes, Woodstock ’99 explores the ill-fated Woodstock revival that took place on a decommissioned, 350-acre military base. The goal was peace and to raise awareness about gun violence, but instead, the attendees embraced chaos and drugs. The crowd faced extreme heat, overpriced food and drinks, excessive trash and waste, and, in the case of the women, sexual harassment and assault. At the same time, the performers were given the red carpet treatment, which further angered the crowd. By the documentary’s end, this all culminated in property destruction, injuries, and multiple fires being set, not only ending the concert on a bitter note, but also tarnishing Woodstock’s legacy in the process.

Money Over Music

Early on, the documentary establishes that Woodstock ’99 was more about making money as opposed to giving attendees a good experience or bringing people together for a worthy cause. Additionally, many of the attendees were more interested in drugs and sex as opposed to love and togetherness, which created a perfect storm for a horrible concert. In terms of production value, the documentary includes interviews with several concert-goers as well as the musicians who performed, giving an interesting glimpse into how and why the concert devolved so intensely. However, at three episodes, Woodstock ’99 is rather long, and it probably could have been condensed into a single movie, like the others on this list, in order to better keep viewers immersed in the traumatic tale.

2

‘The Cult of American Apparel’

With a focus on sexual freedom and ending workplace exploitation, it’s unsurprising that American Apparel took off as a fashion brand (/cult). Founded by Dov Charney, the business quickly attracted “freaks and geeks” who were willing to put in long days and long weeks to ensure the business was a success. However, over time, flaws in Dov’s business strategy—which essentially consisted of yelling at some people and making others feel special—were exposed. Worse, accounts that he had sexually harassed and assaulted his workers emerged. Eventually, most of the employees left American Apparel, and Dov himself was ousted, only to open up Los Angeles Apparel soon after and begin working as CEO of Yeezy.

Lack of Remorse

Many of Dov’s employees had trouble reconciling the man they looked up to with the allegations against him. They also struggled to break free from American Apparel, realizing that so much of their lives were connected to it. Overall, the documentary reveals the perils of workplace abuse and the ways in which seemingly normal individuals can become wrapped up in cult-like conditions. Really, there’s nothing wrong with this documentary, there’s just one on this list that’s even harder to look away from.

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1

‘The Astroworld Tragedy’

Travis Scott’s Astroworld was the concert to be at in 2021. After everything shut down during COVID, music lovers were even more excited to attend, not just because of the amazing acts, but also the atmosphere. Astroworld was known for being chaotic, and during 2021, it was even more so, with people breaking down fences and unticketed fans joining the party, resulting in an already overbooked event suddenly having even more attendees. Horrifyingly, when Travis began his set, one section of fans was so crowded in, that they began to trample and suffocate each other. As the panicked fans tried to escape, the concert continued on, and in the end, hundreds were hurt and 10 were killed, including a 9-year-old and friends of some of the interviewees.

Tragic and Preventable

Astroworld wasn’t just a trainwreck—it was a tragedy, one that still haunts those who attended, and now, haunts us viewers as well. To make matters worse, the tragedy could have been prevented if the proper safety precautions had been taken. In terms of Trainwreck documentaries, this one is the most memorable, upsetting, and viscerally difficult to disengage from. We can only hope that those in the industry have learned from this event and that there will never be a reason for Trainwreck to tell a story like this again.