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Tupac Shakur is said to have once made an attempt to charm actress Lucy Liu while they were working together on the film “Gridlock’d.”

Co-star Bokeem Woodbine shared the story during an interview with “The Art Of Dialogue”, recounting how Pac tried to make an impression on Lucy Liu, who would later gain fame as one of the stars of “Charlie’s Angels.”

Woodbine recalled, “I just remember one day on set, ‘Pac coming to the knock on my trailer. And he was like, ‘Yo, man, what are you doing?’ I was like, ‘I’m just chilling.’ He was like, ‘Yeah, man. I just came back from Lucy’s room and I’m trying to spit game.’”

According to Woodbine, Pac mentioned that Liu offered to teach him martial arts. Shakur reportedly saw it as an opportunity, saying something along the lines of, “He was like, ‘Okay, well, maybe if I feign some interest and act like I’m interested in what she’s trying to talk to me about, it’ll get me closer to sealing the deal.’”

Woodbine shared his amusement over the story. “So, I’m just cracking up. And I said, ‘How’d it work? Did it work?’ He’s like, ‘No, it didn’t work.’ I said, ‘Ah, don’t worry about it, man. You know, you can’t win them all.’”

“Maybe it just went over her head, like, she didn’t know what he [was talking about]. But he was telling me like, ‘Yeah, you know, I’m trying to trying to get to know her and the only thing she wants to talk about is waving these sticks around.’”

In a related anecdote about Tupac’s admiration for other stars, Suge Knight once claimed that the rapper held a deep fascination for singer Aaliyah.

“[He said], ‘I wanna do an album with Aaliyah.’ Pac was so excited. I ain’t never seen that little muthafucka so happy. He wasn’t thinking about signing nobody else. That’s the person he said out of all the girls and women he’d ever seen, he thought she was the biggest star and had the best voice ever.”

“So I figure if things wouldn’t have happened the way they happened, Pac woulda been doing an album with Aaliyah. […] He lost his mind over Aaliyah. He talked about her days and days. I got tired of hearing it.”

Unfortunately, the careers of these two iconic figures never crossed paths creatively before Tupac’s untimely death in Las Vegas in 1996.

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