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Trainwreck: Woodstock '99 is my favorite Netflix show of the year — here’s why

An image from Trainwreck: Woodstock '99 on Netflix
(Image credit: Netflix)

I’m a regular attendee of music festivals, so when I heard that Netflix was set to release a documentary about the infamous Woodstock ‘99 I was pretty intrigued. Just last week, Trainwreck: Woodstock ‘99, dropped onto the streaming service and it’s already become my favorite Netflix show of the year. 

This doesn’t come as a great surprise, one of my favorite Netflix films is 2019’s Fyre: The Greatest Party That Never Happened, and Trainwreck: Woodstock ‘99 definitely has plenty of similarities. After all, both chronicles doomed music events that spiraled into something totally chaotic — but at least for attendees of Woodstock ‘99 the artists actually played. 

I’ve written in the past about my preference for slowly consuming TV shows over a period of weeks, or even months, rather than binge-watching. But with Netflix’s Woodstock docuseries I ended up watching all three episodes in a single sitting. Granted, in total it’s only about two and half hours of content, but I had originally just planned to watch the first episode before finding myself devouring all three. 

Between its fantastic subject matter, and its excellent structure and pacing, I found myself unable to resist hitting the “play next episode” button and then hitting it a second time after that. Netflix has already dropped plenty of big shows this year including Stranger Things season 4 and The Sandman, but for me, this documentary series is the real headline act. 

A trainwreck you can’t look away from 

As you can probably surmise from its title Trainwreck: Woodstock ‘99 recounts the disastrous music festival that was held between July 19 and July 25 1999 in upstate New York. 

Trainwreck: Woodstock '99 image

(Image credit: Netflix)

The event welcomed approximately 400,000 people across the three days and was designed to emulate the original legendary festival that was held in 1969. While Woodstock ‘69 was all about peace, love and flower power, the 90s iteration rapidly descended into total chaos for a wide variety of reasons. 

From extreme price gouging, sweltering 100-degree heat, a lack of toilets/drinking water and a lineup of bands that further riled up the crowd, the festival was a powder keg waiting to go off — and trust me, this thing does eventually explode into a shower of destruction, riots and anarchy. 

Netflix has developed a bit of a reputation for fantastic documentaries, but I’ve recently found myself suffering from true crime burnout. There are only so many docs you can watch about grisly murders and harrowing kidnappings before you start to feel a little disturbed. In that regard Trainwreck: Woodstock ‘99 makes for a nice change of pace. 

That’s not to say the documentary doesn’t explore any series subject matter. The third episode has a segment about sexual assault at the festival and showcases the very worst in toxic masculinity. But I found the series much easier to consume than true crime series releases like The Staircase and new release I Just Killed My Dad

A well-constructed documentary 

Trainweck: Woodstock '99 image

(Image credit: Netflix)

Perhaps I found this docuseries so easy to binge because of its excellent pacing. The three-episode miniseries dedicates a full episode to each day of the festival, and this decision was a very wise one. 

Following the events in this fashion allows you to witness firsthand how events slowly spiraled out of control. The first episode covers the planning of the festival and day one where everyone is in high spirits, the second episode looks at day two when things start to go wrong (and Limp Bizkit whips the crowd into a frenzy) and then it’s in episode three when things really go off the rails. Because of this structure, I felt compelled to watch all three episodes back-to-back just to see what happened next. 

If you’re looking for a new documentary series that will hook you from beginning to end, I strongly recommend Trainwreck: Woodstock ‘99. You don’t even need to have any personal experience at music festivals to enjoy this one either. 

Between its compelling subject matter, zippy pace and slick presentation, this Netflix TV show has set the bar pretty high for the rest of the year. I will be surprised if anything else the streamer releases in 2022 manages to measure up. 

Next: Untold: The Girlfriend Who Didn't Exist is another Netflix doc you definitely need to stream.

Rory Mellon
Deals Editor

Rory is a Deals Editor at Tom’s Guide based in the UK. He covers a wide range of topics but with a particular focus on deals, gaming and streaming. When he’s not scouring retailers for PS5 restock or writing hot takes on the latest gaming hardware and streaming shows, he can be found attending music festivals and being thoroughly disappointed by his terrible football team.