Will Smith and Pepa, from the hit hip-hop group Salt-N-Pepa, could have been rap’s first power couple. In an interview, Pepa, born Sandra Denton, revealed that Smith was interested in dating her.

But in a move, she says she now regrets, Pepa turned down his advances.

This was before Smith was married to his first wife and during his rise up in music circles. Pepa, meanwhile, was enjoying fame as one of the pioneering female hip-hop artists.

Salt-N-Pepa was formed in New York City in 1985 and was composed of Salt (Cheryl James), Pepa (Denton), and DJ Spinderella (Latoya Hanson). DJ Spinderella was later replaced with Deidra Roper. James and Denton met while both were studying nursing at Queensborough Community College. They were also co-workers at the Sears department store. Another Sears co-worker Hurby “Luv Bug” Azor, who was dating James, was studying music production at the Center of Media Arts. He had James and Denton record a song for him as a class project he had to do. The two performed “The Showstopper,” an answer record to Doug E. Fresh’s hit single “The Show.” “The Showstopper” attracted notice from people in the music industry and thus launched the duo’s career.

Their debut album was “Hot, Cool & Vicious. The 1986 album sold more than 1 million copies in the U.S., making them the first female rap act to achieve gold and platinum status by the Recording Industry Association of America, according to Medium. 

Their debut album was followed by 1988’s “A Salt with a Deadly Pepa,” which was certified gold. Then came “Blacks’ Magic,” which featured the mega-hit singles “Expression” and “Let’s Talk About Sex.” In 1993, they released the album “Very Necessary,” which sold over 7 million copies worldwide, making it the highest-selling rap album by a female act (solo or group) in history at the time, Complex reported. The album included the hit singles “Shoop” and “Whatta Man” with the group En Vogue.

Smith hit the music scene as a rapper known as The Fresh Prince with his partner DJ Jazzy Jeff. 

Philadelphia-based Word Records released their first single in 1986, “Girls Ain’t Nothing but Trouble.” Based on this success, Jazzy Jeff & the Fresh Prince were brought to the attention of Jive Records and Russell Simmons. The duo’s first album, “Rock the House,” which was first released on Word Up in 1986, was re-released on Jive in March 1987. The group received the first Grammy Award for Best Rap Performance in 1989 for “Parents Just Don’t Understand” (1988). Their most successful single was “Summertime” (1991), which earned the group their second Grammy and peaked at number 4 on the Billboard Hot 100. Smith eventually made a major splash as a TV actor and then as a film star.

During an interview more than a decade ago with Global Grind, Pepa talked about Smith and the time they used to spend together in the late 1980s. She talked about when the two groups would find themselves together touring.

“I thought Will was really cute, and we would hang out a lot on the road. He liked to take care of me and never let me spend a dime. He was that kind of guy, real generous,” said Pepa, adding that the groups would often compete in hip-hop contests.

“I remember when they won their first award; he asked me to go out with him afterward. He was so excited,” she recalled. She also remembered Smith being generous.

“We were walking along the street getting ready to grab something to eat, and he just gave this homeless guy $100 dollars.”

She admitted she has some regrets about not giving Smith more of a chance at a relationship with her–but he wasn’t her type. 

“I sometimes kick myself when I think about what could have been. He was so nice to me, but I really wasn’t feeling him. I guess I couldn’t appreciate a nice guy like Will Smith. He wasn’t thug enough. I was attracted to thugs and hoodlums. Will was too nice to me,” she shared.

Pepa went on to marry fellow rapper Treach from the group Naughty By Nature. Pepa and Treach remained married for two years, but their tumultuous marriage ended in divorce on July 31, 2001. Smith is currently married to actress Jada Pinkett Smith, having wed more than 20 years ago in 1997. 

Sandra Denton, also known as Pepa from Salt-N-Pepa, arrives at the 10th annual Gold Meets Golden event on Feb. 4, 2023, at the Virginia Robinson Gardens and Estate in Beverly Hills, Calif. (Photo by Allison Dinner/Invision/AP)/Best actor honoree Will Smith attends the National Board of Review Awards gala at Cipriani 42nd Street on March 15, 2022, in New York. (Photo by Evan Agostini/Invision/AP)