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‘It’s a very confusing time,’ the singer recalls (Picture: Ken McKay/Rex/Shutterstock)

‘We’re just anxious messes this generation, aren’t we?’

Seconds after saying hi to X Factor legend Diana Vickers over Zoom, it feels like I’m nattering with an old friend… rather than a singer who was propelled to nationwide stardom 16 years ago.

After spotting ITV’s This Morning playing in the background on her TV, we instantly start chatting about how much we both enjoy rewatching shows for comfort.

‘Sex and the City – I literally start from the beginning, go to the end and then just start again,’ the now 32-year-old remarks. ‘We want to watch things that we know how it ends.’

Well, back when Diana competed on The X Factor at 16 years old, it definitely wasn’t certain how her time in the competition was going to draw to a close.

In 2008, the captivating singer made it all the way to the live shows on the ITV programme, where she was mentored by judge Cheryl in the girls’ category.

Diana was in Cheryl’s girls’ category on The X Factor, alongside the eventual winner Alexandra Burke (Picture: Ken McKay/Rex/Shutterstock)
The singer finished the competition in fourth place at 16 years old (Picture: Ken McKay/Rex/Shutterstock)

She narrowly missed out on a place in the final, finishing in fourth place behind Eoghan Quigg in the third spot, JLS as the runners-up and Alexandra Burke as the eventual winner.

Diana’s elimination resulted in one of the most memorable moments ever seen on the show, when a sobbing Eoghan ran back on stage to hug her while she was singing her farewell song, White Flag by Dido.

It feels like a lifetime ago that The X Factor was at its peak, with Diana going down in TV history for playing a role in one of its most iconic seasons.

While she might be best-known for her angelic voice and ethereal stage presence, she’s now showing off her performance skills in a completely different way, starring as Gwyneth Paltrow in a musical parody of the Hollywood star’s infamous ski trial, titled I Wish You Well.

Before we get to talking about Gwyn and what the Goop founder might think of the play (‘I’d like to think that she is a good time girl and she would totally get it’), we first need to take a trip down memory lane, to the surreal land of reality TV in the late 2000s.

In the years since The X Factor, Diana has released music, appeared in films and TV shows and acted on stage (Picture: Ken McKay/ITV/Rex/Shutterstock)
She’s now set to play Gwyneth Paltrow in a musical parody making its way to the Edinburgh Fringe Festival (Picture: RB/Bauer-Griffin/GC Images)

Diana shares how ‘strange’ she finds it looking back on her time on the programme, admitting that it’s ‘terrifying’ how quickly 16 years have flown by.

‘I just have flashbacks to me sort of being backstage, being absolutely terrified. I was quite a nervous wreck. I mean, I was 16 years old. So there’s absolutely no surprise in that really,’ she recalls.

‘But also just excitement and the possibility of anything can happen. There was just so much going on around me that I didn’t even register at the time.

‘I remember Kate Moss always being there. I used to have pictures of her on my bedroom wall. And then Britney Spears… I kind of took it all in my stride I guess.’

She adds: ‘I was just a baby really. They’re very blurred memories. It’s really weird, for such a crucial time in my life, it’s all just a bit blurred.’

Diana remarks how being 16 years old at the time and coming from a small town in Blackburn made it ‘a lot to digest’ when superstars like Britney and Beyoncé were just casually roaming around on set.

But one of the strangest aspects of the whole experience was going to judges’ houses, when contestants had to endure ‘blacked-out windows’ to maintain the high level of secrecy.

Heading to Cannes for the judges’ houses segment of the competition was a daunting experience (Picture: Fremantle Media/Rex/Shutterstock)
Diana and Eoghan had a very close friendship on The X Factor (Picture: Ken McKay/Rex/Shutterstock)

‘When you go to judges’ houses… I didn’t see any of Cannes,’ Diana says, having travelled to Cheryl’s house in the French city, where fellow Girls Aloud singer Kimberley Walsh made a special appearance as a guest judge.

‘Like literally, you’re sort of in blacked-out windows,’ the singer continues.

‘You get transported from A to B, you’re in someone’s house, but it’s all blacked out in darkness. You can’t really see what’s going on. It’s a very confusing time.’

Diana admits that the nature of being at a judge’s house sent her ‘nervous system’ into a spiral, as it was so tricky to read what the people in charge of her fate were thinking.

‘When you’re at judges’ houses, they don’t give anything away. They don’t say anything. I remember my nervous system being like, “Oh my god.” You become really hyper-vigilant from that show,’ she states.

Another big moment came in the bathroom at the X Factor studio in the UK… when Diana ended up puking in a bathroom due to nerves right next to a 1960s music legend.

Diana explains how nervous she would be before hitting the stage, where her nerves would then dissipate (Picture: Rex/Shutterstock)
On one occasion, Lulu was on hand to help Diana out backstage (Picture: Euan Cherry/Getty Images)

‘[I remember] being sick in the toilet and Lulu being in the same cubicle as me and me being like, “Oh my god, there’s Lulu there,” and I’m vomiting,’ she recollects.

‘She probably doesn’t even remember, but I remember just being so sick and her just being like, “Are you okay?” And I was like, “Yes, Lulu. I’m obsessed with you.”

‘She was really nice. She was very helpful, and she was like, “We love you. You’re amazing.”’

Diana might have ‘struggled a lot with nerves back then’, but she’s now preparing to take to the stage at Edinburgh Fringe Festival with her play I Wish You Well, named after the famous phrase that Gwyneth uttered to Terry Sanderson after he took her to court, accusing her of causing him injury after crashing into him on a ski slope.

After Gwyneth counter-sued, alleging that Terry was the one to crash into her, the actress ended up winning the case and was awarded $1 in damages.

While the Iron Man and Shakespeare in Love actress might not have publicly reacted to the spoof depiction of her court trial, according to Diana, she might have revealed what she really thinks about it.

The ski crash trial took place in March last year (Picture: Rick Bowmer-Pool/Getty Images/The Associated Press)

‘I think she has reacted to it, because I think I know a friend of a friend and I think that she’s just very amused by it,’ Diana speculates.

The singer has high hopes that I Wish You Well could make its way to New York, where perhaps Gwyneth might have a chance to watch it herself.

‘She’s coming across really well,’ Diana insists. ‘We’re being very good towards her. There’s a song that’s just saying how great and funny she was in Shallow Hal and how great she sings in Glee. There’s no hate there, it’s just all love and fun.’

I Wish You Well is the latest instance of the former X Factor star demonstrating her acting acumen, having previously starred in the West End production of The Rise and Fall of Little Voice, played the role of Janet in the touring production of The Rocky Horror Show and appeared in Comedy Central series Give Out Girls.

She also released two studio albums, Songs from the Tainted Cherry Tree in 2010, and Music to Make Boys Cry in 2013.

So what’s next on the horizon?

Diana played Janet in the touring UK production of The Rocky Horror Show (Picture: Dave J Hogan/Getty Images)
The singer has more music in the pipeline, as she’s recently been recording in the studio (Picture: Lia Toby/Getty Images)

‘It’s such an exciting time for me right now. I can’t tell you but I’ve been having exciting meetings and it’s all sort of stemmed from doing my podcast and stepping into me being a bit more open about who I am and the comedy side of things,’ she shares.

‘And my music as well – I have been in the studio again. Everything’s happening, and I can’t really say anything. It’s really annoying. It’s music, it’s definitely the comedy. Everything will hopefully start to come out by the end of the year and next year.’

As our interview begins to wrap up, conversation swiftly switches between various tangents, from Diana revealing that she’s trying to learn how to play the ukulele to how ‘therapeutic’ she finds skateboarding in the park, as well as her passion for Tarot card reading.

‘I’m addicted to reading Tarot. Like, it’s a bit of an obsession. I probably need to stop. I always have them on me. When I go to clubs and stuff, I’ll get them out, and it’s actually made me meet a lot of girly mates. I’ll just start reading everyone’s Tarot at like 12 o’clock in the pub.’

She’s also a massive film buff, so much so that after we say goodbye, she decides to send over a list of foreign movie recommendations, including Benedetta and The Handmaiden.

‘I’m thinking about doing a film club – I’ve got a few people together. I love all that, I’m quite good at that. I’m not good on the book side of things. I quite like a book, but films are my thing,’ she says.

Hopefully that’s a good omen of an I Wish You Well film adaptation in the near future!

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I Wish You Well – The Gwyneth Paltrow Ski-Trial Musical is showing at Edinburgh Fringe Festival on July 31, from August 1 to August 11, and from August 13 to August 26. You can buy tickets here.

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