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‘I Always Had a Thing for Sandy’: Will Smith Recreates Throwback Photo with His Former Crush Sandra Denson of Salt-N-Pepa

Will Smith is keeping it moving while people appear to be concerned about his nontraditional marriage to Jada Pinkett Smith. It seems his new focus is living his best life and getting paid to do so.

The social media darling has just launched his new podcast, “Class of ’88″ — the same year he and DJ Jazzy Jeff became the first rap duo to win a Grammy with their hit “Parents Just Don’t Understand.”

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Considered the most epic year in hip-hop (outside of its founding), 1988 was the year when the likes of Slick Rick, KRS1 with Boogie Down Productions, Big Daddy Kane, Public Enemy, MC Lyte, the Geto Boys, NWA, Audio Two, and Salt -N-Pepa dominated the charts with their most iconic projects, as well as Jazzy Jeff and the Fresh Prince.

Will Smith and Sandra "Pepa" Denton from Salt 'N' Pepa reminisce on their first date.
Will Smith and Sandra “Pepa” Denton from Salt ‘N’ Pepa reminisce on their first date. (Photos: @willsmith/Instagram; @saltnpepaofficial/Instagram)

Smith’s new limited-series podcast lives on podcast apps such as Wondery and Audible. And apparently, fans claim they can already tell the rapper and Oscar-winning actor is having a ball. 

Salt-N-Pepa appeared on the “Class of 88” show, where the old group of friends discussed everything from their childhood in the industry to the time they all boycotted the Grammys in 1989. The female rap group consists of Sandra “Pepa” Denton, Cheryl Renee James, and formerly Spinderella.

The “Push It” rappers said they had more to lose than their male counterparts but knew there was a bigger picture to be gained.

“As women, we didn’t win any awards at that time at all, and as a male-dominated field and taking a chance, we didn’t even know if the Grammys is going to say, ‘You know what? You went against us. You never gon’ be seen.’ But they listened,” Pepa said.

Salt explained that the boycott paid off for the culture, leading to their 1995 win for Best Rap Performance.

Watch the Full Video Here.

The “I Am Legend” actor posted a video clip of himself and the iconic female rap duo decided to recreate a classic picture of the trio from back in the day. Smith captioned the photo, “Some things never change!!”

The same year they boycotted the Grammys is the same year Salt and Smith went on a date. Also on the podcast, they discussed what took place on their one-time date in 1989 when she and her ex-husband Treach of Naughty By Nature were allegedly on a break.

In a clip from episode 6, Smith and Pepa talked about their romantic history and what took place on their one date. He described her as a “special” girl he wanted to impress with his nice car.

“I always had a thing for Sandy but she was always dating somebody else,” said Smith on his “Class of 88” podcast. “I didn’t believe I had a real shot.”

He continued, “So in my mind … I was trying to spit my game, but I ain’t really had nothin’… ’cause my concern was that I was gon’ get killed,” he joked about being scared of the “O.P.P” rapper.

“That was a legit concern,” Salt suggested before the trio broke out into laughter.

Fans took to social media with different takes on the clip. One asked, “Didn’t he used to be in love with pepa?” to which Smith replied, “Nah but the concern was real!! Hahaha.”

Some even referenced the night when the Fresh Prince and DJ Jazzy Jeff refused to participate in the ceremony after learning that the new category of best rap performance would not be broadcast live, despite the two winning the coveted golden gramophone.

“People don’t realize that Will Smith, Salt & Pepa, Public Enemy, Heavy D, and many other legends boycotted because the Grammys didn’t want ‘HIPHOP’ to be a category Let’s Give them their flowers,” one comment read.

Other critics wanted to chime in on his headline-grabbing relationship with Pinkett Smith.

One person commented, “And this is exactly why Jada was cheating,” while another wrote, “Pep said in her book Will was a potential…. Ijs.” A third said, “Jada just threw her phone, hitting poor Willow in the forehead.”

Referring to his former TV girlfriend and “Fresh Prince of Bel-Air” co-star, one person suggested, “Will and Nia Long would have been a better couple.”

For those who didn’t notice, Long played Claudia during the second season of the show. She left and returned as Lisa, Will’s lover, during season 5. Long beat out Smith’s wife for the role of his girlfriend.

The pair never “bumped ugglies,” but Long once described Smith as a “natural-born teacher who lives by his own rules.”

Meanwhile, other commenters noted how “unbothered” he was.

“Will is unbothered he’s more focused on making content for his IG and Tik Tok lol,” one person joked. Another person wrote, with one other saying, “I wanna be this unbothered for the rest of my life.”

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Smith has consistently appeared to be unbothered as the world talks about his secret seven-year separation. He has even joked about not being pressed about the rumors or opinions circulating.

After the release of Pinkett Smith’s “Worthy” memoir, he released an official statement regarding the thoughts of fans, nosy people, and the press. He sneezed. Like the comments said… “Will is unbothered.”

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