In the aftermath of his breakout performance as Bishop in the film Juice, a young Tupac Shakur was plucked by director John Singleton to star as a postman named Lucky in Poetic Justice. The movie shot over a three-month span in California, and co-starred Janet Jackson, at the time one of the world’s biggest pop stars. The experience was, politely stated, a rocky one.
The following is an advanced excerpt from Jeff Pearlman’s Only God Can Judge Me: The Many Lives of Tupac Shakur (Oct. 21, 2025 — Mariner).
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Prior to John Singleton’s focusing on Tupac, the young director’s first choice for leading man had been Ice Cube, the former N.W.A rapper who starred as Doughboy in Boyz n the Hood. It was a brief pursuit—Cube read the script, liked it, but took issue with some elements of the character that Singleton refused to change. Ice Cube was out.
Before making a formal offer to Tupac, Singleton requested that he and Jackson come to Reed’s office for a screen test. It was the first time the rapper and the pop star met, and they seemed to have a nice rapport. They spoke about music, about acting, about the film. Tupac was reserved and warm. “We knew we wanted both, but the chemistry had to work,” said Reed. “I felt like it did. I remember him just being willing to do anything and everything he needed to give all of us the confidence he was right for the part. He made you feel like you were the most important person in the room.”
Later that night, long after his meeting with Jackson, Tupac kicked back with his Oakland crew and—over joints and drinks—told them she was one of the hottest bitches he had ever seen, and he would most certainly have sex with her.
“Bet on it,” he said.
Following two weeks of rehearsal, Poetic Justice shot from April 14, 1992, until July 4, 1992. Along with Tupac and Janet Jackson, the film starred another pair of relative silver-screen newcomers—the actress Regina King (coming off a successful half-decade stint on the TV show 227) and a stand-up comedian, Joe Torry. Initially, Singleton pushed the foursome to become a unit. He wanted them to have dinners and understand the intricacies of one another. “There was definitely a kinship,” said Torry. “Regina, Tupac, and I hung. Janet—not as much. And I think, being honest, it was hard for Tupac. Janet was a star. She was the one with her own trailer, her own this, her own that. A little standoffish. And Tupac also knew that Janet was making a lot more than he was, and it definitely rubbed him the wrong way. He thought they should be equals. She didn’t share that.”
“Tupac definitely did not have warm feelings for Janet,” said Dupré Kelly, a friend and rapper from Lords of the Underground. “I remember him talking about her—‘ I got a car service bringing me to work every day. This chick has helicopters landing her on set. Every day I’m eating chicken and waffles. She’s getting her stuff catered.’ ”
“He made it clear he was pissed about getting less than Janet,” said John Cothran, who played Uncle Earl. “To me, that seemed absurd. Because I didn’t even know who the hell he was.”
Indeed, while Jackson was pulling in seven figures, Tupac made less than a hundred thousand dollars. For much of shooting, the cast was lodged at the Loews Santa Monica, and Tupac was placed in the smallest available room (Jackson had a suite). “There were about five of us Black employees,” recalled Lesa McRoyal-Fouther, a reservation desk manager, “and they’d always send one of us to ask Tupac to turn down his music or lighten it up with the marijuana smoke. Other guests were complaining.”
From a talent standpoint, the Janet-Tupac financial gap was unjustified. For all her stage presence, Jackson was a one-note actress. She arrived on time, remembered her lines, but brought little to the table. Tupac was the opposite. He was the best part of the movie—“ Every scene he’s in, he owns,” said Jenifer Lewis, the actress who played the mother of Tupac’s character, Lucky. But he was also chronically late and unwilling to memorize his lines. Once, in a unique display of chutzpah, he arrived an hour behind schedule to film a highly anticipated love scene with Jackson. The middle of his chest was covered with a large, gooey piece of gauze. When asked the cause of the injury, Tupac lifted the paper to reveal a new tattoo—one he had had done (impulsively) the previous night. It read “50 niggaz,” atop a rifle. Singleton was apoplectic, and told Tupac the tattoo not only violated his contract but made the scene tricky to shoot.
“What am I supposed to do?” asked the director.
“Fuck if I know,” Tupac replied, then stormed off to his (tiny) trailer.
According to Torry, as the days passed, Tupac’s attention waned. His tardiness increased from a few minutes here and there to a few hours several times per week. He not only failed to memorize the script, but tried ad-libbing far too often. He was high all the time, drunk some of the time—and it showed. As a musician, being impaired can inspire creativity. As an actor, it lends itself to sloppiness. “He was usually ready when he got to set,” said Cothran. “If he got to set.”
Though not in Tupac’s class as an actor, Jackson was a pro’s pro—a by-product of spending almost two decades in the spotlight, and knowing what it meant to have a crew of people depend on you. Predictably, she was turned off by Tupac, by his approach, by his weird efforts at being sexual, by his need to always steal attention. He was a child in a man’s body. It all felt like some sort of act—an insecure kid trying to prove his worth. It was exhausting.
Shit hit the fan late in the process, when it was time to film a kissing scene. In the days beforehand, Tupac talked nonstop about overwhelming Jackson with his lips and tongue. He thought he was being cute. She did not. Three days before the sequence was to be shot, Nicolaides was summoned to Jackson’s trailer, where she sat with her fiancé, a dancer named René Elizondo Jr. “You know, Tupac’s reputation is that he’s a cat about town,” Jackson said. “And I don’t want to swap saliva with him until I’m really sure that he’s healthy and clean.”
“OK,” Nicolaides replied. “Have you talked to John about it?”
Jackson looked disgusted. “John just walked off when I mentioned it,” she said. “So I’m asking you to handle it.”
The forty-three- year- old Nicolaides did not relish what was to follow.
He had worked on a bevy of high-profile films, including When Harry Met Sally and The Princess Bride, and knew all too well the wrath of an actor’s ego. He took a couple of deep breaths and walked over to Tupac, who was sitting alone in his trailer
“Sooooo . . . Tupac,” he said.
Tupac looked up.
“I’ll just spit this out to you, man,” he said. “Janet wants you to have an AIDS test before you kiss her.”
“You kidding?” Tupac asked.
“No,” said Nicolaides.
“Fuck her,” Tupac said. “I ain’t doing shit for that bitch. Tell her to go fuck herself.”
“Um, OK,” Nicolaides said. He prepared to leave, and Tupac flashed a big smile.
“So . . . you’ll do it?” Nicolaides asked optimistically.
“Hell no,” Tupac replied.
“I honestly think he found it amusing,” Nicolaides said. “And the truth is, I can’t blame Janet for asking. It was the early 1990s, and people were still dying of AIDS. And Tupac, God love him, had a reputation.
“But he never got the test.”
Copyright © 2025 by Jeff Pearlman. An edited excerpt from the forthcoming book Only God Can Judge Me: The Many Lives of Tupac Shakur by Jeff Pearlman to be published by Mariner Books. Printed by permission.)
