How do you follow up what’s generally regarded as the greatest music documentary ever made? For a long time, it was a question that Madonna: Truth or Dare (or, as we knew it in the UK, In Bed With Madonna) director Alek Keshishian had no intention of answering.

The controversial and groundbreaking documentary, released in 1991 after the pop star's Blond Ambition World Tour a year prior, not only changed the way filmmakers explored the world of celebrity, but also had a profound impact on LGBTQ representation in film. This was a mainstream release that took a non-judgemental approach to homosexuality, a real rarity in the early Nineties. Truth or Dare won accolades, going on to become the highest-grossing documentary of all time before it was beaten in 2002, but Keshishian, who was 25 and a recent Harvard graduate at the time of filming, effectively retired from documentaries. One and done, it seemed.

Now, over three decades on from his genre-defining debut, he’s finally back with a second documentary. The subject is Selena Gomez, in the highly candid Selena Gomez: My Mind & Me. On the face of it, Madonna and Gomez are very different subjects: one, a brash, unapologetic singer who lives for the limelight and still thrives on courting controversy; the other, an ex-Disney star who shot to uneasy levels of global fame as a child, who has been troubled by health and mental health issues as an adult singer and actor. So what was it about Gomez that convinced Keshishian to take on the job?

preview for Selena Gomez My Mind and Me - Official Trailer (Apple TV)

“It was a very interesting evolution,” he reveals over a Zoom call from LA. “It was actually never meant to be a documentary”. Back in 2015, Keshishian’s sister was representing Gomez, and she revealed that the singer was obsessed with Truth or Dare. She had watched it seven times in a row and would love to meet him. After initially brushing her off (“Selena Gomez, she’s like what, some Disney girl?” he remembers) he met up with her. “She was so real and vulnerable,” he says. “I kind of fell in love with her.”

Gomez, at the time, wanted to change her image. Alongside appearing in Harmony Korine’s edgy Spring Breakers in 2012, she thought Keshishian would be the perfect person to help her shake off her House of Mouse persona. A music video followed, the suggestive Hands To Myself, in which Gomez plays a stalker who breaks into an actor’s house and rolls about his bed in her underwear. The collaboration went so well (440 million views on YouTube) she asked Keshishian to document her 2016 tour, Revival. He turned her down. “I said no, because for 30 years I’ve been asked to do that and I’ve always said no,” he says. “One of the reasons I always said no to documentaries was because I was so spoiled with Truth or Dare, Madonna let me shoot anything. I became her right hand. No one told me 'don’t come into this room'. I told Selena, ‘I don’t think you’re prepared for the way I shoot’.”

Still, she persevered. A two-week test shoot followed and Keshishian presented Gomez with a five-minute piece of how the documentary might look, and her reaction made him even more certain of his decision. “She was like,‘It’s beautiful, but can you not show me crying and can you not show me mentioning that’. I said, ‘This is what I’m saying, it’s not time for you to make a documentary. Certainly not with me’. Her record label Interscope said, ‘Will you still do it?’ and I said ‘No, that’s not what I do and I’ll be fine never doing another documentary again’.”

Cut to November 2022, and Keshishian’s second-ever documentary is about to stream on Apple TV+. Here’s how one of Instagram’s most followed stars (current count 354 million) got Keshishian on board, and what he makes of the three decades of celebrity culture between his two films.

What made you finally relent to Selena?

Well, Selena had captured a place in my heart, and because of my sister, I would see her a lot and she became a bit like one of the family. In 2019, after she came out of the mental facility, I saw her afterwards and I was filled with hope for her, and I had this great feeling of empathy. I was asked to go and shoot her in Kenya for a charity trip for their website and I said of course. But on the first day of shooting, something happened.

What happened?

I was like, ‘Wow, this is a documentary’. It was the same feeling I had in Truth or Dare when I went to Japan [with Madonna] and I was just meant to get a little bit of backstage stuff and I started doing those interviews and I was like, wait a second, there’s a documentary here! It’s not the show, it’s what’s happened behind the scenes. For the first hour of filming we were going to McLean Hospital and Selena was getting an award [for people who have raised awareness about mental health] and I was like, this is a girl who has just come out with her diagnosis, she’s still very much in recovery herself but she wants to use it to help other people. There’s a connection there and that’s how it started.

Madonna and Selena seem like polar opposites. Did you see any similarities between the two?

I think they’re very different people and I’m a very different person, too. I was 25 when I made Truth Or Dare and I think that was like a lightning-in-a-bottle moment. Madonna loved her celebrity and fame and what she could do with it. She was brave and a beautiful soul and it was so exciting to be with her, I fell in love with her and I think she fell in love with me. One of the reasons I probably don’t like to do documentaries is that I fall deeply in love with my subjects. But ultimately, they’re two incredibly brave women, so in that respect there are similarities but in every other respect they’re very different.

Do you think it was easier to be a pop star back then or now?

I think it’s harder and easier. Back then there were three big globally known people: Madonna, Michael Jackson and Princess Diana. That was it. The means of information was A.M. radio, that’s how Asia and Africa and remote corners of the world were interacting. Today we have this very fractured landscape where you have hundreds of pop stars - the true closest to a global superstar is someone like Selena, who goes above and beyond being a pop star. But now you can be a pop star and have a very successful career and have a relatively small following. It’s just a different world.

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Also, Madonna wasn’t plagued by social media.

Yes, this was a very specific time before social media. [Because of this] when the documentary started happening one of the first things I said when I was speaking about this [was]: ‘Selena’s the most reluctant pop star I’ve ever met’.

That’s definitely the impression you get in the documentary. That level of fame seems not only to be making her miserable, but making her ill. Did you ever think of suggesting that she just give it all up?

She has this conundrum [of her fame and philanthropy]: you have to do this in order to have the platform to do that. It’s that conundrum that she faces. For Selena it’s not about going to the coolest restaurants. She loves her fans, I’ve never witnessed someone who came so alive interacting one-on-one with human beings.

There’s a particularly upsetting scene when she meets a girl in Kenya and there’s a discussion about suicide. Selena says: “I really relate to that… where you’re about to do something to hurt yourself”. Did you take that to mean it was also something that had crossed her mind?

I think she was in a sense saying: ‘I have had moments like that’. The thing with Selena is she really listens. You don’t have to be a pop star with a giant platform to connect with people, sometimes it’s just enough to listen to somebody’s else’s story to be there, to bear witness. I think that’s what she’s about. She shows you how simple it can be – just two women talking. It's just a simple act of friendship that can happen between any two people.

You shot Truth or Dare in black and white, and then there are certain scenes in My Mind & Me also shot in black and white. What was the creative decision behind that?

In Truth Or Dare everything was shot in black and white because I wanted to show the difference between backstage and onstage. It was used much more for impact or contrast to the colour. The black and white is a bit more brutal in My Mind & Me, like her breakdown sequence; it goes to black and white and I remember telling my colourist to make it more aggressive and more contrast-y. I was trying to let you experience almost what an episode would feel like for Selena, like where the world becomes black and white, anger, frustration, so it was used differently to bring out her emotional experience.

With Truth or Dare, is there one scene that you’re particularly proud of or one that stands out to you as being important, 30 years on?

I have not watched Truth or Dare for so many years. I tend not to watch my stuff. Last time I watched it was with Madonna in the Museum of Modern Art for the 25th anniversary, so we both watched it for the first time in 25 years and we were like, ‘Who made this?’

new york   may  1991  susanne bartsch’s love ball 2 at the roseland ballroom in may 1991 in new york city, new york  pictured madonna and alek keshishian  photo by catherine mcganngetty images
Catherine McGann//Getty Images

Did the fall out from Truth or Dare – in which three dancers sued for "invasion of privacy, fraud and deceit, misrepresentation, and intentional infliction of emotional distress", followed by an out-of-court settlement and the lawsuit dismissed – impact on you at all?

This is where it goes beyond my pay-grade. All those dancers signed contracts when they became Madonna’s dancers and I don’t know the legalese but I think they all worked it out. I saw the dancers at Outfest and I hugged them, so for me, it’s all good. Unfortunately sometimes business and legalese happens and my mind just doesn’t work at that level.

So the lawsuit wasn’t what put you off making other documentaries?

No, not at all. I just realised soon after Truth or Dare that all these people wanted me to do documentaries, I was like, but now you know the secret and you’re going to try and control it!

Who did you say no to. Can you name any names?

No, but you can imagine…

I imagine everyone must have come running to you after that.

To a certain degree. Truth Or Dare was a very specific time and once it came out people were like, ‘Oh, we can do that, but I want to control it more’ and I just don’t do well being controlled.

Madonna asked you to direct her second documentary, 2005’s I’m Going To Tell You A Secret, but you said no. How come?

We talked about it, and I said: ‘I don’t see how that’s a documentary because really what’s interesting are your kids, and as your family, if we shoot that it’s going to feel exploitative to your kids and if we don’t shoot it, then what’s the documentary really about?’ I just didn’t see eye to eye… I didn’t feel there was a documentary I could contribute to.

Would you ever do another documentary with Madonna now?

I don’t think that’s really on the cards.

Are you still friends now?

We don’t text or email or are in constant contact but I did see her a few weeks ago in New York. I hugged her, I still love her, I love what she’s done for so many communities, for women, for gay people, and I still have a great deal of affection for her but no, our lives are very, very different now.

Truth or Dare almost became the genesis of reality TV with its now ubiquitous confessional interviews. How do you feel about that?

I am so sorry! I feel terrible because I think reality TV is so not real and the irony was Truth or Dare was so real but like anything, when you try to formulate it it becomes the opposite of what it was originally, which is why I haven’t ever done that. Cinéma vérité is a very patient way of filming something, I shot 250 hours of film for Selena; reality TV, they have like a five-day shooting schedule so they create those scenarios and the beats. They’re kind of the opposite of each other even though on the surface they seem similar.

Who would be your dream subject for another documentary?

I think that Lil Nas X is really interesting and is pushing the envelope in so many, really important ways. I think he’s a real artist, there’s something going on there that's being channelled from like… I don’t mean to sound all weird, I do believe he’s doing something that is changing the world. For me, at the end of the day, I’m less interested in pop stars than I am in people who are trying to change the world.

Selena Gomez: My Mind & Me streams on Apple TV+ from November 4.