When a 17-year-old Tupac Shakur walked into Leila Steinberg’s living room, she sat up and took notice.
For one thing, the aspiring rapper was supremely talented, elevating her weekly poetry circles with his exquisite verses and poignant phrasings.
Then there were the pirouettes and pliés, his outlandish persona and his look: pink eye shadow, black nail varnish and, once, a full cheerleader outfit.
‘I’d never met a person like Tupac,’ said Steinberg, a community activist and ‘elder sister’ to the Bay Area high school students.
‘He was so unique and outside the box. I initially assumed he was gay, because he was extremely feminine. Everything from his mannerisms to doing ballet in my living room.’
In fact, she said, ‘I do believe, nowadays, he would have defined himself as fluid.’
Almost 30 years after his murder, Tupac still manages to surprise.
Now, a new book, ‘Only God Can Judge Me,’ has revealed a remarkable hidden side to the gangsta rap pioneer and his complicated relationship with his own sexuality.
According to friends if Tupac Shakur was alive today he would define himself as ‘fluid’
Steinberg is one of the many close friends who spoke to the author, Jeff Pearlman, to reveal that the man with ‘Thug Life’ tattooed across his stomach was actually flamboyant, sensitive, bookish and even ‘effeminate’ before he became a famous rap superstar.
Born in New York City to a Black Panther mother who rapidly descended into crack addiction, Tupac had a transient childhood, moving in 1984 to Baltimore, where his mother, Afeni Shakur, had relatives.
Encouraged by an artsy, white, liberal couple who lived next door, in 1986 theatrical and curious Tupac auditioned for and was accepted by the prestigious Baltimore School for the Arts.
Tuition was free for city residents; those outside Baltimore paid $15,000 a year for the opportunity to study alongside future stars of Broadway and Hollywood.
Jada Pinkett-Smith, future wife of Will Smith, was in Tupac’s class, and the pair were close.
Another classmate was Seth Bloom, who described himself in the book as ‘a gay theatre kid’.
He and Tupac hit it off so much so that, Bloom told Pearlman, there was a frisson between them, beyond friendship. He recounted how at a party they were drinking tequila shots and were dared to kiss each other.
‘He kissed me,’ said Bloom. ‘We kind of vamped it up, our lips touched. I know I wasn’t the only boy Tupac kissed.
‘When we were alone, I always felt a thing. You know that sexual tension where you hold a glare a second or two too long, or you touch someone longer than normal? That was Tupac.
‘My belief is he was somewhere between heterosexual and bisexual.’
Tupac thrived at the school – wildly popular and successful with the girls but also loved longingly by the boys for his mischievous, outlandish ways.
‘He kissed me,’ said Bloom. ‘We kind of vamped it up, our lips touched. I know I wasn’t the only boy Tupac kissed.’
Tupac, pictured above in the 1988 Baltimore School of Arts yearbook. The rapper thrived at the school where he was popular and successful with girls and loved longingly by boys.
Yet within two years of joining BSA, he was forced to leave: his mother Afeni kicked the then-17-year-old Tupac out of the house and shipped him across the country to live with family friends in Marin City, in the Bay Area of California.
Tupac enrolled at Tamalpais High, where he met Steinberg and her artistic entourage.
‘He was so different than most of the kids from Marin City,’ said Chava Bramwell, a white classmate who spoke to Pearlman. ‘Honestly, it was strange for us to see a black kid like him.
‘He was in touch with his feelings. He was feminine and soft and sweet and gentle. Really, he was effeminate. Very effeminate.’
Liza Monjauze, another classmate, told how she and Tupac went to the mall together to get both ears pierced. Tupac spray-painted his own clothes, and bleached blonde a strip of his hair, which Monjauze said was ‘really confusing.’
And La Donna Bonner, also in Tupac’s class, told Pearlman how for the 1988 ‘Spirit Week’ – an annual celebration of the school’s culture – Tupac dressed in a full cheerleader outfit, complete with the skirt and pompoms, and paraded through the cafeteria.
‘I asked around – “Excuse me, who is this crazy boy? And what has he been smoking?”‘
On graduating, Tupac’s nomadic existence continued. He bought a house in Atlanta but was drawn back to his native city of New York – breaking hearts wherever he went. His womanizing was legendary – and devastating.
In November 1993, 19-year-old Ayanna Jackson, whom he had met in a nightclub, accused him of raping her at a Manhattan hotel with two other men.
Tupac denied the charges but was convicted of sexual abuse and sent to Rikers Island for a month. An eight-month stint at Clinton Correctional Facility in upstate New York followed. Just 20 miles from the Canadian border, it was nicknamed Siberia for its harsh conditions: the rapper was there from Valentine’s Day of 1995 until October that same year.
Wendy Williams, then a radio shock-jock, claimed that Tupac was raped in prison by fellow inmates, something he denied in a 1995 interview with the Los Angeles Times.
He said it was hard ‘watching the media report all kinds of lies about me, like that I got raped in jail. That never happened.’
Tupac’s womanizing was legendary and devastating. In November 1993, 19-year-old Ayanna Jackson, whom he had met in a nightclub, accused him of raping her at a Manhattan hotel with two other men.
Tupac was convicted of sexual abuse and sent to Rikers Island for a month. An eight-month stint at Clinton Correctional Facility in upstate New York followed.
What is undeniable is that Tupac made a series of surprising friends while behind bars.
Not least, his cell mate, described by Pearlman as ‘a flamboyant gay man,’ who cooked up tomato soup in their cell and shared it with the rapper.
Another man with whom Tupac formed a close bond was a corrections officer, who wrote a 2021 book about his experiences inside prisons under the pseudonym Michael Christopher.
Christopher took an interest in Tupac’s writings and became something of a therapist to the rapper as he talked through his traumatic, poverty-stricken childhood and told of his absent father and dysfunctional mother.
When Tupac was freed, he signed a photo for Christopher, writing: ‘To a good man. I wish you all the success in the world.’
He also became good friends with Joey Fama, an Italian American convicted for the murder of a young black man in Brooklyn, who, Pearlman writes, became ‘briefly the face of bigotry in the Big Apple’.
And college student Shannon Siegel, who like Fama was white, and convicted of almost beating to death a black man he saw talking to a girl he was dating.
They were, writes Pearlman, ‘men he certainly would not have hung with on the outside.’
But then, for Tupac, his public persona and private reality were two very different things.
Shot dead in Las Vegas following a fight with a rival LA-based gang, he died on September 13, 1996, at the age of 25.
Three of the four people in the car that pulled up alongside Tupac’s vehicle that night, spraying it with bullets, are dead.
The sole survivor, former gang leader, Duane ‘Keffe D’ Davis, will go on trial in February.
