Tupac Shakur in 1994.

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Tupac Shakur wasn’t always the cool, stylish and tough figure who came to define 1990s hip-hop. As a teenager, he was awkward and eccentric. He wore braces over his gapped, slightly brown teeth and walked like a duck, exhibiting a self-conscious swagger that made him stand out for all the wrong reasons.

But even then, Shakur was magnetic and drew people in — a charm that, as writer Jeff Pearlman argues in his book Only God Can Judge Me: The Many Lives of Tupac Shakur, helps explain the contradictions that shaped Shakur’s short, extraordinary life.

“When people give too much grandeur to his thoughts and his behavior, both negative and positive, actually, I would say you have to remember, he was a baby, like he was a baby,” Pearlman said.

Shakur was 19 years old when he began working on his debut album, 2Pacalypse Now, and only 25 when he was shot and killed.

“He didn’t know what he was doing. He was trying his best,” Pearlman said.

A longtime sportswriter and New York Times bestselling author, Pearlman has chronicled baseball legends, football stars and unforgettable seasons in the sports industry. But he wanted to try something new.

Pearlman interviewed over 600 people for his latest book, including Tupac’s high school girlfriend, who shared more than 100 love letters Shakur had written to her, crack dealers in Marin City, Calif., who informed his sound and perspective, and the baby who inspired one of his most memorable songs, “Brenda’s Got A Baby.”

What Pearlman found through these conversations and extensive research was a man of “yin and yang,” a person of constant dualities: sensitive yet hard-edged, sexualized but inexperienced on the subject of intimacy, and a devoted son who struggled to watch his mother develop a crack addiction.

Pearlman spoke to NPR’s A Martínez about Shakur’s personal life, from birth to his early 20s, and how it shaped his incomparable career and led to his devastating early death.

Here are three takeaways from the conversation.

Tupac’s mother was a hero but not a mom

The book begins with a 21-year-old Afeni Shakur attending the 1970 Panther 21 trial, where several members of the Black Panther Party in New York were accused of shooting at police officers and attempting to destroy police stations. Afeni, then pregnant with Tupac, turned down a court appointed attorney, because she didn’t think the attorney was loud enough. With little money and a high school education, she represented herself — and won.

“I feel like we should have been, for years, learning about her in the history books in American history classes,” Pearlman said.

Tupac was proud to call Afeni his mother. He bragged about her role as a Black Panther and held on tightly to her early lessons of strength and Black pride. But their relationship grew complicated as she fell into a serious drug addiction.

“So, you have this guy who worships his mother and tells everyone he meets, ‘Oh, my mom was a Black Panther. My mom, Panther 21, my mom represented herself.’ And then at the same time has the sadness and the heartbreak of watching her fall into a state of what seemed to be disrepair,” Pearlman said.

Later in his music career, Tupac released a song — a classic in the hip-hop world — titled “Dear Mama,” which describes a single mother struggling to raise two children on welfare. In the song, Tupac is candid about his mother’s crack addiction, but he intertwines difficult lyrics with direct affirmations to his mother, repeating things like, “You are appreciated.”

Pearlman found the song was more aspirational than autobiographical.

“He had a hero, but he didn’t have a mother,” Pearlman said.

A sex symbol who didn’t understand sex

By the time he became a famed rapper and a working movie star, he was widely seen as an American sex symbol.

But Pearlman found that image was not rooted in reality. In fact, he says, Tupac “didn’t understand sex” — at all.

“He was 14 years old when he had his first sexual experience, and it was with a cousin,” Pearlman said. “Then when he was 15 years old. He had his second sexual experience and it was with a friend of his mother, an adult friend of his mother.”

Tupac Shakur performs at the Regal Theater in Chicago, Illinois in March 1994.

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Tupac Shakur performs at the Regal Theater in Chicago, Illinois in March 1994.

Raymond Boyd/Getty Images

With no father and little guidance, Tupac grew up not understanding intimacy and how to sustain emotional connections, especially with romantic partners, according to Pearlman.

Tupac lost a rap battle — it ignited his career

Raised in New York City and later Baltimore, Tupac attended Baltimore School for the Arts, where he wrote love letters and poetry and participated in theater. But, before his senior year of high school, his mother moved the family across the country to Marin City, Calif., where his music career developed and soared.

At 17, kicked out of his mother’s house, Shakur moved in with DJ Shaboo, Demetrius Striplin, who supported Tupac and introduced him to the local hip-hop scene. Tupac jumped in showing off his writing and storytelling skills, and, eventually, he started battle rapping other musicians in the city.

“One day Tupac does a rap battle in Marin City in front of a bunch of people, and there’s a 13-year-old rapper named Tac. And Tac just demolishes him. And Tupac is devastated,” Pearlman said.

Tupac disappeared for several days after the battle.

During his short-lived hiatus, he shadowed a local gangster for inspiration. Tupac studied how he walked, talked and thought, and when he returned to Striplin’s house, he wrote “Days of a Criminal,” a song about life as a California gang banger.

“The song is awesome,” Pearlman said. “And that was Tupac getting his butt kicked and realizing, ‘I can’t just rap about my thoughts. I have to rap about what I see and what is going on around me.’ And that was the moment, sort of a really key moment, for Tupac.”

In that moment, Tupac had found the formula for his music and discovered the persona that he wanted to embody.

Like many moments in the late rapper’s life, he overcame hardship or devastation and turned it into gold.

The start of Tupac’s career was defined by the same tension Pearlman traces throughout his book: the artist and the fighter, the proud kid yearning for his mother, and the young man the world turned into a mogul and, ultimately, a myth.

The audio story was produced by Kaity Kline and edited by Lindsay Totty. The digital version was edited by Majd Al-Waheidi.