In a surprising revelation on his Class of ‘88 podcast, Will Smith, the multifaceted actor and rapper, shared details about his “one and only date” with Sandra “Pepa” Denton of Salt-N-Pepa during the late ’80s. The revelation unfolded during a nostalgic conversation about their paths to rap stardom.
Smith, 55, confessed that he had harbored a crush on Pepa for a long time but finally seized the opportunity for a date in early ’88. Reflecting on his efforts to impress her, he rented a white Mercedes convertible and planned a picturesque evening driving around Hollywood Hills, culminating in watching the sunset.
However, the date took an unexpected turn when they encountered a homeless person, and Smith, in a surprising move, handed the person $100. Pepa fondly recalled this gesture, emphasizing its kindness. The duo then proceeded to the iconic Hollywood sign, creating lasting memories.
While Pepa appreciated the efforts, Smith revealed his inner turmoil during the date. “My concern was that I was going to get killed,” he admitted, confessing to feeling terrified while trying to impress Pepa. He humorously added, “That might have been the most terrified I had ever been trying to shoot my shot with Pepa. And I didn’t believe I had a real shot.”
Despite the brief fling that ensued, Smith highlighted the enduring camaraderie between him, DJ Jazzy Jeff, and Salt-N-Pepa. The actor reminisced about their amicable relationship even after the romantic spark dimmed.
This revelation adds a charming layer to the dynamic between Smith and Pepa during the vibrant ’80s hip-hop era. The Class of ’88 podcast continues to offer insights into the early days of rap, with Smith sharing anecdotes about industry figures like Rick Rubin and his experiences on the road.
In the broader context of hip-hop’s 50th anniversary this year, Salt-N-Pepa expressed astonishment at the enduring success of their careers, emphasizing the genre’s powerful impact and the ongoing love and embrace it receives from fans.
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