Simon Cowell reveals he tried to get hit track Hit Me Baby One More Time for his band Five

Simon Cowell has revealed he offered a songwriter a Mercedes to give his band Five the now-hit track Hit Me Baby One More Time, but it had already been promised to Britney Spears.

The record executive, 62, said he told Swedish producer Max Martin that ‘no one is going to have a hit with the name Britney Spears’ as he tried to bag the 1998 track.

He said he was desparate to get Hit Me Baby One More Time – which was originally penned for TLC – for his own boy band Five, as he was sure it was going to be a hit.

Speaking on the Howie Mandel Does Stuff podcast, Simon said he even went as far as to offer Max a flash Mercedes in exchange for what became a chart-topping track.

But Simon explained that he sadly ‘missed out’ on the song as Max, who has penned songs for Katy Perry and the Backstreet Boys, said he had already promised the song to Britney, which became her break into the music industry. 

Simon explained: ‘I had a boy band at the time called Five, who I’d put together, we were just on the verge of breaking them from America. 

‘Someone phones me from America and says I’ve just been played this song. It was written for TLC, and he played me down the phone to me and was like, ‘oh my God, I’ve got to have this song’. 

‘So I phoned up Max and said ‘please, please give me this song’. And he went, ‘I’ve promised it to someone else’. And I said, ‘well I’ll send you a Mercedes 500 SL if I can have this song’. 

‘And he went ‘no, I’ve promised it to somebody else’. And I said ‘who?’ and he went, ‘Britney Spears’. And I said ‘Max, let me give you some advice, no one is going to have a hit with the name Britney Spears’. She wasn’t even known.’

Despite missing out on the song, which went on to top the charts in 22 countries, Simon said Max made the ‘right decision’ in keeping his promise to give the song to Britney. 

‘He’s honourable. He promised the song and he wasn’t going to break the promise, and look, he made the right decision,’ he said.

‘We’re still good friends now, listen I would have taken the car! And don’t forget, no one had heard of this girl before so he was not going to break his promise. So I missed out on that, but that’s how we met and became friends.’

Elsewhere on the podcast, Simon spoke about the first track and music video he released in the music industry – a song called So Macho by his then-girlfriend Sinitta.

Speaking about his romance with Sinitta, Simon said they started dating before she shared her aspirations to become a singer, and then they decided to make her first record together.

‘I met her, and I liked her, we started to date and then she told me she wanted to be a singer, and I heard some demos, and I went ‘well, I’ll make the record’,’ Simon said.

The entrepreneur explained that he was only given around £3,500 from the label he was working for to create the record and the video, and he decided to take on the challenge.

He explained: ‘The video cost me £1,500, I had to manufacture the record. It took me a year and a half to break the record and it went to number two in the charts, it sold a million copies, so that was my first hit.’ 

However, the record company then went bust and Simon was encouraged to sell his shares, saying he was ‘completely and utterly broke’ and owed the bank $500,000 when the firm folded.

Simon said he was forced to sell his house and his Porsche and had to return to living back at home with his parents, but said he was very lucky that he found someone who had faith in his career after his hit with Sinitta.

He explained: ‘I was about 27/28. I was very lucky, I found a bank manager who believed in me and he said ‘I’ll give you a loan and you’ve got to pay it back to me because if you’ve done it once, you’ll probably do it again, so I’m going to back you’. 

‘It took me about four years to pay everything back, but it was interesting because everything I thought I loved – my stupid Porsche or my house – I couldn’t care less, I gave it back. My mum and dad were thrilled, they never wanted me to leave in the first place.’

Speaking about his relationship with Sinitta, Simon revealed he is still good friends with her and she also gets on with his fiancee Lauren Silverman.

‘She is like still one of my best friends. You can still like your exes,’ he said. 

Simon has previously enjoyed high profile relationships with the likes of Sinitta, Jackie St. Clair and Terri Seymour and has remained close friends with his former flames.

Simon and Sinitta famously dated in the 80s when she was signed to his label, Fanfare Records, and had an on-off relationship for 20 years.

In 2020, Sinitta suggested her on-off romance with Simon was ‘never really over’ until he had son Eric with girlfriend Lauren in 2014.

When asked when her and Simon had ‘finally called it quits’ on their love affair, the singer, 58, told New! Magazine: ”There was always an element of ‘well, it’s never really over.”

‘But when Eric was born that was it. I would never come between his family.’

The X Factor creator met his now-fiancee Lauren when she was still married to millionaire property developer Andrew.

Their affair famously became public and Simon’s life changed at the end of July 2013 when news broke of Lauren’s pregnancy with their son Eric.

Simon popped the question on the couple’s Barbados getaway over the new year in front of their son Eric and Lauren’s son Adam.

Despite Simon’s previous staunch vows to never walk up the aisle, an insider recently claimed the past two years – in which the global pandemic hit and the star broke his back after a bike crash – made Simon change his stance.

Simon previously admitted that he can’t see himself ever dating again as he opened up on changing his mind about marriage after falling in love with Lauren.

He said he decided to propose to his long-time girlfriend in January after feeling like they were already engaged while living together during lockdown.

He described the Covid-19 pandemic as a ‘make or break’ moment for relationships and said lockdown helped him and Lauren to grow closer and realise how much they get on.

He told The Sun: ‘I also just couldn’t see myself ever dating anyone again. The idea of going out on a first date now is too weird.’