The California Love rapper met his tragic end after a drive by shooting in Las Vegas in 1996, but just two years before that he enjoyed a steamy romance with the world’s biggest popstar.

The fling passed many fans by at the time, but a break-up letter penned by the rapper to his lover while he was serving time in prison in 1995 confirms they had been together – and as it circulates online once more after three decades, it’s leaving people stunned.

Though the Vogue songstress posthumously outed their relationship during an interview with Howard Stern 20 years later, it was Tupac’s ink to paper about the ‘magic’ they shared that has captivated fans’ attention.

Close friends and family have long labelled the star a ladies man who dated several famous women before his untimely death, including Jada Pinkett Smith and Jasmine Guy.

In the emotional letter, which he penned when he was 23 years old, he wrote that he ‘never meant to hurt’ Madonna, but feared that his love for the ‘extremely famous sex symbol’ could derail his already shaky career.

Though at the time Tupac was a bonafide rapstar, he was serving a stint at New York’s largest prison, Rikers Island, following a conviction for first-degree sexual abuse.

This along with a string of other controversies – including a public spat with Janet Jackson over her alleged request for Tupac to take a HIV test before kissing her in 1993 film Poetic Justice – had left his promising career on the rocks.

Tupac relished a steamy – albeit secret – romance with the Queen of Pop in the mid 90s (Pictured: Madonna and Tupac at a Vogue magazine party in 1994)

It appears the public failed to catch on at the time, with news of their fling – and its sour demise – confirmed only by a stinging three-page letter the rhymer wrote to Madonna from prison in 1995. (The ex-couple are pictured seemingly leaving a Vogue party together in 1994)

The then 23-year-old rapstar wrote a breakup letter (pictured) to Madonna, at the time age 36, from Rikers Island prison in 1995

He made the chilling decision to ditch Madonna, then 36, blaming ‘racism’ and their 13-year age gap, which he said made him ‘scared’.

Tupac, the son of late political activist Afeni Shakur who was a member of the Black Panther Party, said he felt ‘society’ made it ‘difficult’ for a ‘young black male to properly show affection for an older white woman’.

Save a few telling photos of Tupac and Madonna cosied up together at a Vogue magazine party in 1994, the details of their love affair have been scant.

Fans have had to settle for Tupac’s heartfelt letter to the Queen of Pop as the last remaining remnant of one of the most unlikely couplings of the century.

The letter was first revealed to the world in 2017 when it was uncovered by TMZ, which stated Tupac had ‘dumped’ Madonna because she was ‘white’.

But a closer look at the letter indicates the decision was more complex than meets the eye, and one the rapstar said he ‘struggled’ to come to terms with.

Tupac made the chilling decision to end things with Madonna, blaming ‘racism’ and their 13-year age gap, which he said made him ‘scared’

In the letter to his former flame, he poured his heart out, writing that he ‘never to meant to hurt’ the popstar

On January 15, and while incarcerated at the maximum security facility in The Bronx, New York, Tupac – born Lesane Parish Crooks – penned:

‘I’ve waited a long time to finally write this, mainly because I was struggling to find all the answers so that I wouldn’t leave any unanswered questions’.

He then referred to Madonna as a ‘friend’ and ‘apologized’ for not being the kind of companion ‘I know I am capable of being’.

‘Not because I am evil’ he insisted, ‘or because you weren’t worthy’.

He continued: ‘At the risk of sounding over dramatic, the effects of racism make it difficult for a young black male to properly show affection for an older white woman.

‘For you to be seen with a black man wouldn’t in any way jeopardize your career, if anything it would make you seem that much more open and exciting.

‘But for me at least in my previous perception I felt due to my “image” I would be letting down half of the people who made me what I thought I was’.

Tupac was serving a one-and-a-half to four-and-a-half year stint at Rikers Island, following a conviction for first degree sexual abuse

Rikers Island (pictured), in The Bronx, is New York’s largest and most feared prison

Pouring his heart out, Tupac continued to say he was ‘stuck’ on Madonna but ‘got scared’ by their connection.

‘I didn’t want to be a “toy” or another one of many’,’ he penned.

He said he discovered Madonna’s romantic past after listening to an interview she had given, and claimed his ‘ego’ was hurt by it.

Throughout the 80s and 90s, the Like A Virgin hitmaker was linked to a string of male celebs such as Sean Penn, Vanilla Ice, Dennis Rodman and even Michael Jackson.

Tupac stated in his letter that he had been ‘cut deep’ by learning Madonna had been with lots of other stars.

‘It was at this moment out of hurt and a natural instinct to strike back and defend my heart and ego that I said a lot of things I have since come to regret,’ he said – suggesting the pair had had an argument.

He then said a ‘f***ed up’ society stopped the couple from dating ‘openly’, and was the primary reason they were forced to keep things private – culminating in their eventual split.

While burning a flame for the Grammy-winning songstress, Tupac was in fact married, and rumoured to be entertaining a plethora of famous beauties including Jada Pinkett (The duo pictured in 1996)

A Different World actress, Jasmine Guy, was also close with the rapstar and visited him during his incarceration

Tupac’s bravado often preceded him; he was famed for flamboyant and flirtatious tracks like 1994’s Temptations and 95’s Picture Me Rollin.

However hits like Changes and White Man’Z World – both posthumously released in the 90s – alluded to his deeper thoughts on classism and race.

In addition, his heartfelt hit, ‘Dear Mama’, an open letter penned in the 90s to his mother Afeni Shakur, revealed a sensitive side to the rapper.

‘You always was a black queen, mama… I finally understand for a woman it ain’t easy tryin’ to raise a man’, he passionately rapped.

Afeni was a political activist and a member of black power movement, Black Panther Party, founded by then-college students Bobby Seale and Huey P. Newton in 1966 in Oakland, California.

Born Alice Faye Williams, Afeni changed her name when she joined the movement. She was later famously accused of being involved in a plot to bomb a number of public buildings.

The late activist was pregnant with Tupac in 1971 when she was jailed for the alleged crime and while she and other Panthers faced conspiracy charges. The charges were later dropped.

Throughout his life, Tupac spoke openly of his mom’s fight for ‘black power’. He also rapped about growing up both poor and black, which he felt negatively affected his upbringing.

At the time, Tupac’s success was no match for Madonna’s superstardom, multi million record sales and unending accolades. He perhaps referred to this by calling her an ‘extremely famous sex symbol’ in his letter (Pictured: Madonna at the 1985 American Music Awards)

Throughout the 80s and 90s, the Like A Virgin hitmaker was linked to a string of male celebs, such as former basketball great, Dennis Rodman and Michael Jackson. Tupac said her romantic history ‘cut’ him ‘deep’

He was later convicted of the first-degree sexual abuse of a woman named Ayanna Jackson in December 1994, and was sentenced to up to four-and-half years in prison – although he only spent nine months behind bars.

He maintained his innocence up until his death in 1996.

Perhaps the rapper’s sombre prison stint afforded him time to reflect on his past, as he insisted in his letter that he had grown ‘both spiritually and mentally’.

Pleading with Madonna to understand where he was coming from, he wrote: ‘Please understand my previous position of that of a young man with limited experience with an extremely famous sex symbol – who also happens to be known by every man, woman and child in the world’.

In 1995, Tupac made history as the first ever recording artist to have an album debut atop the Billboard 200 while incarcerated, a feat he achieved with his emotionally charged third album, ‘Me Against The World’.

Still, his success was no match for Madonna’s superstardom, multi-million record sales and unending accolades.

So one question on inquiring minds is how the Hip Hop bad boy and Queen of Pop met and how it all started.

Actress Rosie Perez introduced the star-crossed lovers, and later boasted that she played matchmaker to her ‘good friend’ Tupac and Madonna.

Speaking on The Drew Barrymore Show in November last year, the White Men Can’t Jump actress, now 60, narrated the surreal tale.

In the letter, Tupac wrote that not everything came down to ‘color’ and that he appreciated Madonna’s kindness during his ‘craziness’, and hoped they could still be friends (The star pictured performing in Chicago in 1994)

Actress Rosie Perez later revealed she played matchmaker to her ‘good friend’ Tupac and Madonna in 1993 (Pictured: Rosie Perez and Tupac Shakur at the 7th Annual Soul Train Music Awards in Los Angeles in 1993)

She told how she set the stars up while she herself was on a date with Tupac at the 7th Annual Soul Train Music Awards in 1993.

Rosie revealed that Tupac sweetly offered to accompany her to the event after her date bailed on her a ‘half an hour’ before she was set to leave for the award show.

‘I’m gonna go with you. We’re gonna walk up in there, we’re gonna act like we’re on a date and he’s going to die’ said Tupac comfortingly over the phone.

Ultimately, the actress said she ran into Madonna, who asked if her and Tupac were a couple.

After explaining they weren’t, Rosie said the Material Girl singer asked her to ‘hook’ them up. Perez, replied: ‘You got it!’

Similarly, fellow ex Deathrow records collaborator, Snoop Dogg, recounted the moment he spotted the ex-lovers together just before a music performance.

According to Rolling Stone, in 2018 the Gin and Juice rapper told radio host Howard Stern that a request to his friend to bring him a ‘big bag’ of w**d resulted in the surprise sighting.

‘Guess who he [Tupac] pulls up with?’ Snoop Dogg asked the host. Snoop then launched into a hilarious rendition of Madonna’s 1984 monster hit ‘Like a Virgin’.

‘[Tupac] was showing me that he was elevated in the game’ the star added.

But their affair would be short lived, and after dating for a little over a year, Tupac decided to end things, though he hoped Madonna would remember the ‘good times and magic we shared’.

Tupac was convicted of the first-degree sexual abuse of a woman named Ayanna Jackson in December 1994, and was sentenced to up to four-and-half years in prison – although he only spent nine months behind bars. (Ayanna Jackson pictured in 2018)

Tupac’s upbringing as the son of late political activist and member of now-disbanded black power organization, Black Panther Party, Afeni Shakur, could have contributed to his decision to end things with Madonna

Further along the letter, he wrote that not everything came down to ‘color’ and that he appreciated Madonna’s kindness during his ‘craziness’ and hoped they could still be friends.

‘Now my outlook is different – everyone is judged and treated not by their color or fame but on how they treat me’ wrote Tupac.

‘And because you have been so kind even in the midst of my craziness – I offer my friendship once again… this time much stronger and focused.

‘If you are still interested I would like to further discuss this with you, but some of it couldn’t wait’.

‘I felt compelled to tell you…just in case anything happened to me’ he added.

Things took a more cryptic turn when Tupac asked the superstar to ‘be careful’.

‘Please be careful Madonna. Everyone is not as honorable as they seem. There are those whose hearts bleed with envy and evil’ he penned.

It’s no secret that the rapper’s lyrics and personal life were intertwined, with gun violence nearly taking his life before the fatal drive by in 1996.

In November 30 1994, while in an elevator at Quad recording studios in New York, Tupac was shot five times during a bungled robbery which he miraculously survived.

A chain of events would set off the infamous East Coast/West Coast feud, as the rapper publicly blamed New York native, rapper Notorious B.I.G, for the ambush.

Tupac seemingly alluded to this in the letter, writing ‘They [people] would not hesitate to do you harm! Let my five bullets be proof of that!’

He followed this up with a request for information regarding ‘Jack and crew’ – supposedly Jaques Agnant, a Haitian-born music executive nicknamed ‘Haitian Jack’ – who Tupac also suspected was involved in the shooting.

Though neither Madonna or Tupac have admitted to a secret rendezvous at Rikers Island, court documents obtained by DailyMailTV in 2017 may indicate otherwise (The popstar in LA in 1994)

He made reference to this in his critically acclaimed posthumous album, The Don Killuminati: The 7 Day Theory, released two months after his death in 1996.

‘It could very well be a matter of life and death’ he continued in the lengthy letter.

He concluded the note with an impassioned plea for his now ex-flame to visit him in prison – ‘If you could find it in your heart I would love to speak face to face with you.

‘It’s funny but this experience has taught me to not take time for granted’ he wrote.

Though neither star has ever admitted to a secret rendezvous at Rikers Island, court documents obtained by DailyMailTV in 2017 suggest the singer may have paid her former flame a visit.

After receiving the personal letter, Madonna possibly left her New York City apartment, stationed just a few miles from Rikers Island, to visit Tupac.

In a deposition, Madonna, then 59, acknowledged that she had read and received the letter from Tupac while she was staying at her apartment.

But the musician skirted around the question of whether or not she visited the rapper while he was locked up, stating: ‘I’m not answering that question’.

When the lawyer pressed further on the visitation matter, she curtly responded: ‘It’s not relevant to this letter’.

The same year the singer filed an emergency court order to stop the auction of Tupac’s letter, which court papers revealed was expected to fetch up up to a whopping $400,000.

The Material Girl stated she was ‘shocked to learn’ of the planned online auction of the letter and had no idea it was no longer in her possession.

In 2022, Madonna took her daughter Mercy James to an exhibition honouring Tupac Shakur’s life

The items were consigned to auction by Darlene Lutz, a woman Madonna described in court documents as a former friend and art consultant, who she said had ‘betrayed my trust in an outrageous effort to obtain my possessions without my knowledge or consent’.

The singer said her ex-pal had access to her home on numerous occasions as an overnight guest, alleging that some of the items, such as the hairbrush, were taken without her permission or knowledge.

‘I understand that my DNA could be extracted from a piece of my hair. It is outrageous and grossly offensive that my DNA could be auctioned for sale to the general public’ she said in court papers.

‘The fact that I have attained celebrity status as a result of success in my career does not obviate my right to maintain my privacy’.

The auction was hosted by Gotta Have It! Collectibles and in July 2017 a judge initially halted the sale and that of the singer’s other personal items.

Manhattan state Supreme Court Judge Gerald Leibovitz ordered Gotta Have It! Collectibles to pull the personal items from its rock-and-roll-themed auction.

However in 2019 Madonna lost the appeal to halt the auction, with the New York State Appeals Court ruling the star can’t sue her former friend Darlene Lutz for selling the letter to an online auction house.