“I never would have imagined that this video would become a tangible memory, of the last time Pac and I, were simply kids together,” she wrote via Instagram.

Will Smith and Jada Pinkett

Will Smith and Jada Pinkett at the Blockbuster Awards on February 11, 1997. Getty Images

Will Smith’s “Parents Just Don’t Understand” is one of those songs that will always resonate with each new generation. For some, like his wife, Emmy-winning actress and talk show host Jada Pinkett Smith, the song holds myriad memories. On Wednesday (Sept. 20), Pinkett Smith shared an adorable throwback video of her and the late Billboard Hot 100-topping rapper Tupac lip-syncing to Smith’s 1988 hit single.

“Not in a million years would I have dreamed that the Fresh Prince and I would become, um, very acquainted. Not in a million years did I imagine three lives, their fates, would be so intertwined,” she wrote in a lengthy caption. “And… I never would have imagined that this video would become a tangible memory, of the last time Pac and I, were simply kids together. Pac and I lip syncing Parents Just Don’t Understand by Jazzy Jeff and the Fresh Prince during our Junior year in high school. Who would have thought?”

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The caption appears to be an excerpt from a chapter from Worthy, Pinkett Smith’s forthcoming memoir. In the clip, she dons a collection of gold chains, a black top and grays shorts as she lip-syncs and dances along to the song with Pac, who sports a blank sleeveless tank, black shorts and similar gold chains. Era-appropriate hairstyles and visual effects help round out the vintage clip. In a second post, Pinkett Smith joked that the pair did a “terrible job” lip-syncing.

Smith, as one-half of the hip-hop duo DJ Jazzy Jeff & The Fresh Prince, released “Parents Just Don’t Understand” as the second single from 1988’s He’s the DJ, I’m the Rapper. The song peaked at No. 12 on the Hot 100, and won the inaugural Grammy for best rap performance. Under her first post — Pinkett Smith limited the comments of the second clip — DJ Jazzy Jeff commented, “Absolutely amazing.”

Since Pac’s unfortunate passing in 1996, Pinkett Smith has often relived her memories with him in front of the public. In 2017, she revealed that she was a drug dealer when she first met him, and in 2021, she shared an unpublished poem from the “Dear Mama” rapper. While Pac was alive, Pinkett Smith appeared in his “Keep Ya Head Up” and “Temptations” music videos, and covered $100,000 for his bail after he was convicted for sexual abuse. While the two stars never officially dated, their incredibly close friendship has become a point of public debate, especially in light of her and Smith’s “entanglement” controversies — hence the feisty comment section under the first throwback clip.

Worthy is slated for an Oct. 17 publication date.

Check out Jada Pinkett Smith’s throwback Tupac clips below: