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Review: Trainwreck: Woodstock ’99 (2022)

Trainwreck: Woodstock ’99 (2022)

Directed by: Jamie Crawford

Premise: A documentary about the 1999 Woodstock music festival. The three-day show famously descended into chaos and was replete with vandalism, looting, and assault.

What Works: For viewers who are unfamiliar with the infamous Woodstock ’99 festival, this documentary provides an overview of what happened with a mix of archival footage and contemporary interviews. Split over three episodes, Trainwreck goes into detail about each day of the festival. Woodstock ’99 is a case study in event mismanagement and how failure to adequately plan for the realities of the show produced a catastrophe. The most illuminating aspect of the documentary is the interviews with behind-the-scenes personnel. The senior leadership are defiantly adamant that they are not responsible for the rioting or assaults or general misery of the festival but the lower-level employees recall key decisions that led to the final result.

What Doesn’t: Trainwreck: Woodstock ’99 is the second documentary about the 1999 music festival in as many years. In 2021 HBO Max premiered Woodstock 99: Peace, Love, and Rage and that documentary was better. Peace, Love, and Rage covered all of the important topics addressed in Trainwreck but the HBO documentary also contextualized the festival. It compared Woodstock ’99 to the two previous incarnations of the concert especially the original Woodstock and the way our cultural memory of that concert has been distorted by nostalgia and the famous concert documentary. Peace, Love, and Rage also connected Woodstock ’99 with the state of the culture at that time. Trainwreck is about an hour longer than Peace, Love, and Rage but the Netflix documentary doesn’t make use of that time and in fact misses some important details. Namely, Trainwreck makes no mention of the deaths that occurred at Woodstock ’99. (Three people died. Peace, Love, and Rage addresses one of them.) Trainwreck also does a disservice by obfuscating the cause of the riots and abuse. The senior festival organizers interviewed in the documentary strenuously argue that the crowd and the musicians were to blame for the chaos but it is obvious that the key factors at Woodstock ’99 were the horrendous environmental conditions and the price gouging for food and drink. The filmmakers of Trainwreck don’t take the side of the festival management but this documentary does give the impression that responsibility is shared equally between the concertgoers, the musicians, and the organizers. The documentary also dishonestly casts the loutish and abusive behavior by male concertgoers as a thing of the past when it clearly is not.

DVD extras: Available on Netflix.

Bottom Line: For viewers who are unfamiliar with Woodstock ’99, Trainwreck offers a summary of what happened but viewers would be better off seeking out Woodstock 99: Peace, Love, and Rage instead. The longer film actually has a narrower scope and omits important details. 

Episode: #914 (August 21, 2022)