Even legends strike out sometimes.
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In a recent interview with Art of Dialogue, actor Bokeem Woodbine shared a hilariously sweet memory of Tupac Shakur attempting—and failing—to charm his Gridlock’d co-star Lucy Liu while filming.
Although Shakur is widely remembered as one of Hip-Hop’s most magnetic and bold personalities, this story proves even legends can strike out sometimes.
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“I just remember one day on set, ‘Pac coming to knock on my trailer,” Woodbine began. “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.’”
But the stunning actress, who was apparently practicing with escrima sticks (a traditional Filipino martial arts weapon), was more focused on her training than on Tupac’s charm.
Lucy Liu attends the Hudson River Park Annual Gala at Cipriani South Street on October 17, 2019 in New York City.
Jamie McCarthy/Getty Images for Hudson River Park
“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 recalled.
Unfortunately for Pac, the plan didn’t pan out. “So, I’m just cracking up,” Woodbine said. “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.’”
Actor Bokeem Woodbine attends the Vanity and FX Annual Primetime Emmy Nominations Party at Craft Restaurant on September 17, 2016 in Beverly Hills, California.
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Pac confessed to Woodbine that Liu wasn’t “vibing” with him “in that kind of way.” Woodbine added, “Or 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 get to know her and the only thing she wants to talk about is waving these sticks around.’”
Despite the missed signals, Liu remembered Tupac fondly in a 2023 interview with The Sydney Morning Herald, saying, “He was nice and we had a great time together. It’s so strange to think that he’s gone now.”
Lucy Liu attends Storytelling Summit: Lucy Liu during the 2025 Tribeca Festival at Spring Studios on June 08, 2025 in New York City.
Manny Carabel/Getty Images for Tribeca Festival
Gridlock’d, released posthumously in January 1997, was one of Tupac’s final film roles. Co-starring Tim Roth, Bokeem Woodbine, and Lucy Liu, the comedy-drama follows a pair of heroin addicts trying to get clean while navigating the chaotic bureaucracy of the rehab system.
The film was modestly successful at the box office and was critically praised for showcasing Tupac’s versatility as an actor.
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Woodbine, who also appeared in Tupac’s “I Ain’t Mad At Cha” music video, remains one of the few to share such personal, lighthearted glimpses of a side of Pac many never got to see.
