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In Bed With Madonna documentary
In Bed With Madonna documentary

8 essential pop star documentaries to watch immediately

Ahead of Taylor Swift’s Miss Americana dropping on Netflix, here’s the films every serious pop stan needs to see

‘There is only one thing in the world worse than being talked about, and that is not being talked about,” Oscar Wilde wrote in The Picture of Dorian Gray, cutting to the core of celebrity culture way back in 1891. The trappings of celebrity and the froth of fame can still overtake reality, but today stars fling a version of themselves into every digital portal to keep the conversation going. The clout of celebrity offers unique opportunities and audiences, but Wilde’s eventual exile speaks to the danger of being misjudged, of how the cult of personality can supersede truth. Plus, Wilde’s aphorism came long before social media – these days, anyone in the public eye is going to be talked about, whether they want this or not. 

In the midst of that high-volume media, pop documentaries have the unique opportunity to break, augment, or reinforce the prevailing, preconceived narrative about the artist in question. The latest attempt at threading that needle is Taylor Swift’s Miss Americana, landing on Netflix this Friday (January 31).

Directed by Lana Wilson, the documentary looks at the star’s career in the midst of her fight against a radio DJ who groped her (and the ensuant lawsuit) and steps into political speech (her support for Democrats in Tennessee congressional races, despite concerns this could alienate her fanbase). Swift is unlocking the influence she can wield in the real world. Marketed as a look at Swift without the filter of perfection, Miss Americana aims to act as an emblem of not only the person, but the personality that Taylor Swift has become.

As much as pop music is about the song, it’s also about the narrative. In preparation of Miss Americana’s release, we’ve assembled a list of eight key pop documentaries that demonstrate the universe from which the film has sprung, focusing exclusively on narrative documentaries of the pop genre and its stars.


Too often, vulnerability is tied to fragility. Opening oneself up to criticism doesn’t necessarily mean waiting to be cut down – as seen in In Bed With Madonna. On one hand, Madonna is baring all on-stage, and on the other, she’s mock-vomiting as Kevin Costner exits her green room, mortified by his unenthusiastic praise of her show as “neat.” Madonna narrates the film, but her partner at the time, Warren Beatty, suggests that she’s not the type to hide anything: “She doesn’t want to live off-camera,” he smiles. Ever the leather red-lipped harbinger of things to come, Madonna-as-narrator presages the social media age. In Bed With Madonna looks at an artist eagerly offering themselves to the public eye with no filter – or their own filter, depending on perspective.


From The Kinks to Oasis, bands featuring brothers have not always ended well – throw in the spectre of the House of Mouse and you have the ingredients for something explosive. The Jonas Brothers’ Chasing Happiness spends plenty of time in the fluffy sweetness of their prepubescent heyday, and even more on how satisfied they are in their 2019 reunion, but the former purity ring sweethearts also dig into the venom that led to their split. There’s added intrigue in their high-profile partners (Game of Thrones star Sophie Turner and Indian actress/singer Priyanka Chopra), plus the sordid details of their hiatus (Kevin Jonas’s reality show irking his brothers, frustration at a few less-than-platinum singles, Joe losing his passion for music, and more). The tears, anger, and betrayals feel so fresh, no matter how much gloss they might drop over it – making it a perfect example of the tricky tightrope between presenting an ideal and sharing the real. Despite the happy ending, the angst feels about as raw and unexpected as a hunk of tooth-spinach caught on live TV.


Amy Winehouse suffered from the attention thrust upon her. Amy is the only documentary on this list released after the artist’s death, offering a different perspective of the most trying moments of Winehouse’s career and life. While other documentaries needed to cut away the ideal and reveal the painful reality, Winehouse’s struggles were unfortunately always out in the open. The tabloids had been cruel to pop stars before, but Winehouse’s life was cut tragically short at a powerful convergence: the internet allowing for both constant media coverage and for the music industry to widen outside of tight machine control. The film brims with raw, previously unseen footage detailing Winehouse’s drug and alcohol abuse, self-harm, bulimia, and fraught relationships – but also plenty of proof of her unrivaled art. Amy is a document of not only the star’s life and death, but also the havoc that the modern world can wreak on artists – a reminder of how obsession with celebrity and a lack of proper mental health and addiction provisions can ruin a life.


In the heart of Gaga: Five Foot Two, Stefani Germanotta offers a succinct assessment of her career: “I want to do the opposite of what everyone thinks I’m going to do.” Early on, this meant head-turning outfit choices, the era surrounding 2016’s Joanne was one of unvarnished simplicity and honesty – or at least, the perception of it. Gaga: Five Foot Two, released in the Joanne era, is, like Gaga’s art, indebted to the women that came before her, both literally and artistically – namely her conversations about never getting recognition from Madonna, and others honoring her family, including her aunt Joanne who passed away as a teenager. The moment Gaga reads through Joanne’s poems and looks at her artwork is as affecting as any in the star’s career. Beyond a compelling fly-on-the-wall moment, Five Foot Two acts as a precursor for the Oscar-nominated emotional depth around the corner.


The sparkling image of the Disney brand has acidified and faded since the days of the Mickey Mouse Club, but the current crop of now-adult pop stars revealing their struggles is chipping away at the last remnants of wholesome prestige. While the Jonas Brothers’ Chasing Happiness exposed the familial infighting behind the Disney veneer, Demi Lovato: Simply Complicated digs into the star’s bipolar disorder diagnosis, her biological father’s physical abuse and substance abuse, and her own addiction issues. The 2017 doc even goes so far as to undercut a previous film, 2012’s Demi Lovato: Stay Strong, which discussed her time in rehab and recovery. Simply Complicated reveals that she was under the influence of cocaine even while being interviewed for the earlier film. Over 80 minutes, Simply Complicated is a fascinating demythologisation of fame, money, Disney, pop music, and even documentaries themselves.


The internet is full of Britney Spears conspiracy theories, a majority of which tied to the conservatorship she’s under, overseen by her father Jamie. The #FreeBritney crowd has been advocating for her ‘freedom’; some are merely concerned by the relative obscurity of the situation, while others sense secret messages in her blink patterns in Instagram videos. But long before the hashtag, Britney: For the Record detailed Spears’ comeback and all of the personal trauma that led to the viral moment in which the pain that had been building up under label-defined facade of the pop star perfection became too much. While we may all remember the shaved head and umbrella, watching a young woman who has gone through too much too fast describe her life as like “when you go to jail” or like “Groundhog Day every day” brings that memory from wacky meme to horrific tragedy. It may not sate the conspiracists still certain Spears is being held captive (it feels at times like an hour-long version of her Instagram stories), but For the Record looks at the tragic surreality that a former megastar now inhabits.


For every Justin Timberlake, there are at least five other boy band members relegated somewhere beyond the footnotes of music today. Once at the absolute top of the world, the five members of the Backstreet Boys sunk away rather quickly. They were time-stamped from their inception: no one stays a boy forever. Whether it was the group growing out of their popularity or their brand of pop burning out of favour, Show ’Em What You’re Made Of offers plenty of humanity and context to that pivotal moment. In the betrayal of boy band puppetmaster Lou Pearlman and the members’ various stories of hardship, the film successfully does away with the bravado that announced their arrival and reveals the Boys as they were, rather than how we were meant to see them.


Ever the mold-breaking queen, Life is but a Dream stands out because of Beyonce’s utter artistic control. It takes a rare talent to act as co-writer, co-director, executive producer, narrator, and star simultaneously; and while the resultant documentary may not be a raw revelation behind the scenes, it’s a paean of Beyonce’s genius. It’s not necessarily only a document of her life, but rather a document of her artistic mind. Full of straight-to-laptop-camera empowerment speeches and lush celebration of her unparallelled passion, the film is a fascinating look at the nature of control in the social media era. While other artists push thoughts through Twitter and family photos through Instagram daily, Beyonce has carefully and successfully cultivated an artistic representation of self despite those pressures. “How much do I reveal about myself?” she asks – and Life is but a Dream is a fascinating look at that decision-making process. There may never be a “real” documentary about Beyonce in her lifetime; while it’s a blessing to have a pop star with this artistic composure share her own perspective, a look at that process from just outside of her frame could be life-changing.