When Kriss Kross Launched a Backward Clothing Trend

Good looks and the right gimmick can take you far in the music business, but throw in a great song—something the average person might still be able to recite from memory three decades later—and you’ve got a recipe for ridiculous levels of success. This is one lesson to be gleaned from the story of Kris Kross, the teen rap duo that ruled the world for a little while in the ’90s.

Featuring rappers Chris “Mac Daddy” Kelly and Chris “Daddy Mac” Smith, Kris Kross rose to international fame with their infectious 1992 debut single, “Jump.” It took just four weeks to reach No. 1 on the Billboard Hot 100, and it propelled their debut album, Totally Krossed Out, to the top of the Billboard 200. In less than a year, the LP went quadruple platinum.

“Jump” was a super-catchy song built on samples of several songs, including The Jackson 5’s “I Want You Back,” and when the “Jump! Jump!” part of the chorus hit, it was virtually impossible to keep your feet planted. And then there was the duo’s look: Smith and Kelly rocked mega-baggy jeans, baseball caps, and oversized sports jerseys—all worn backward.

Kris Kross managed to avoid becoming a one-hit wonder. Their second album, 1993’s Da Bomb, went platinum, while 1996’s Young, Rich & Dangerous, their third and final LP, went gold, spawning one last Top 20 hit, “Tonite’s Tha Night.” But changing tastes and the natural life cycle of artists meant that the pair’s time in the limelight was brief. 

When Chris Kelly died of a drug overdose on May 1, 2013, at the age of 34, it had been years since most people had thought about Kris Kross. And yet news of his passing instantly made millions of thirty-somethings nostalgic for the days when the Mac Daddy and Daddy Mac had everyone airborne. 

Made In the Mall

Chris Kelly and Chris Smith met as first graders in the Atlanta area. “We’re twins who don’t look like each other,” Smith told The New York Times in 1992. They grew to be close friends with a shared love of hip-hop, rapping along to records by Eric B & Rakim and Run-DMC. While they were interested in show business, they never really thought it was possible—until one day when they went sneaker shopping at the Greenbriar Mall and spotted the local female rap trio Silk Tymes Leather.

Smith and Kelly asked for an autograph and immediately caught the eye of the group’s producer, Jermaine Dupri, an ambitious music-biz climber whose father had been road manager for the likes of the S.O.S. Band and Cameo. Dupri couldn’t help but notice everyone in the mall staring at the well-dressed preteens as if they were already famous.

“I had never seen no little kids look like me,” Dupri told The Washington Post. “That’s what it was. They had on almost better gear than me. Almost. Fresh new sneakers. I was like, ‘Wait a minute. How old are these kids?’”

Dupri took the boys’ phone numbers, even though they told him they didn’t really rap and only sort of danced. He was convinced they had star quality, and over the next couple of years, he began cultivating their talent as rappers. In Dupri’s estimation, their skills “went from terrible to excellent,” and in the spring of 1991, he landed them a deal with Ruffhouse Records, a label distributed by Columbia. 

Ruffhouse boss Joe Nicolo was apparently impressed by “Lil’ Boys In Da Hood,” a song about the harsh realities of inner-city life, as experienced by a couple fresh-faced kids who could rap without cursing.

Totally Krossed Out

Dupri wrote and produced almost all of the boys’ debut, Totally Krossed Out. It took him about two years, though he admits to spending only 30 minutes on “Jump,” the song that would make Kris Kross a global phenomenon.

“It was an idea to try to create a call-and-response record, something that everybody could be a part of,” Dupri told Complex in 2013. “They were kids, and I knew that it needed a thing to attach to it. It was an overall idea. I saw everybody jumping at most of the concerts at this time of me going to concerts. It was like, I should make a song about what I see.”

The last piece of the puzzle was the group’s style. In interviews, Kelly and Smith said they worked with Dupri to develop their everything-backwards aesthetic, the “totally krossed out” look, as they called it. (Angela Smith, Chris’s mother, told The Washington Post that she came up with the duo’s name, as she remembered that a teacher used to call Kelly “Chrissy Crossy Apple Saucy” because he only ate applesauce.)

“Kris Kross means up is down, left is right, and the inverse is the adverse,” Smith told The New York Times. “That’s who we are. That’s why we wear our clothes this way.”

That look was on full display on March 29, 1992, when Kris Kross delivered a spirited performance of “Jump” on the popular Fox sketch comedy show In Living Color. The single had been out since February and failed to make much noise, but buoyed by the prime-time TV appearance, it debuted at No. 61 on the Billboard Hot 100 and shot to No. 12 the following week. Two weeks later, on April 25, it was the No. 1 song in America.

Even critics were on board. Robert Christgau, the so-called “Dean of American Rock Critics,” praised “Jump,” calling it “one of those works of art that makes rock and roll worth living for, a trifle that sweeps all questions of import and integrity aside.” “Jump” wound up placing third on The Village Voice’s prestigious Pazz & Jop year-end critics poll.

“Jump” remained at No. 1 for eight weeks, during which time Totally Krossed Out topped the Billboard 200 album chart for two nonconsecutive weeks. The album yielded a second Top 20 single in “Warm It Up,” and in June 1992, Michael Jackson released his “Jam” music video, which featured a cameo by Kris Kross. The duo joined the King of Pop on the European leg of his Dangerous World Tour that summer.

A Side of Beef

A minor subplot in Kris Kross’s rise to stardom was their involvement in a four-way beef involving fellow Atlanta heartthrobs Another Bad Creation, a.k.a. ABC; Philly upstarts Da Youngsta’s; and the duo Illegal, featuring Mr. Malik, a cousin of Snoop Dogg. In the opening verse of “Jump,” Kelly raps, “Don’t try to compare us to another bad little fad,” which was a blatant jab at ABC. 

In April 1993, Da Youngsta’s hopped into the fray with “Crewz Pop,” featuring the anti-Kris Kross line: “​​I pray for the chump that bumps me or plays me like a punk / So jump, jump if you want me.”

Kris Kross fired back in August 1993 with “Alright,” featuring Smith rapping, “See, I ain’t come out wack I came out right / Unlike those moles who tried to ‘Pass Da Mic.’ ” (“Pass Da Mic” was a Youngsta’s single from 1992.) Also in 1993, Illegal dropped “We Getz Busy,” in which Mr. Malik mentions Kris Kross by name and chides them for rapping words they didn’t write: “Can’t write ya own rhymes, sellin’ Jermaine’s life stories.” 

Malik later told 4080 magazine that he and his bandmate, Jamal Phillips, got into a fistfight with Kris Kross at MTV personality Ed Lover’s birthday party. Whatever happened, Kris Kross lived to fight another day, and the other groups more or less faded into obscurity. 

Jumping Back to Earth

Rap fame in the ’90s could be incredibly fleeting (see: MC Hammer and Vanilla Ice), but Kris Kross stuck around longer than some might have expected. With their 1993 sophomore album, Da Bomb, the teens adopted the West Coast hip-hop sound popularized by Dr. Dre and turned in a slightly more mature collection of songs. The single “Alright,” featuring Jamaican dancehall artist Super Cat, cracked the Top 20 on the Billboard Hot 100, and the album went platinum. 

The duo followed it up with 1996’s Young, Rich & Dangerous, featuring the single “Tonite’s Tha Night,” which reached No. 12 on the Hot 100, their highest placement since “Jump.” The track “Live and Die for Hip Hop” features vocals from Aaliyah, and while the album only went gold, Jermaine Dupri praised it years later in an interview with okayplayer.

“Those are hood-classic records on that album,” Dupri said. “I feel like when we make music or rap records, we always try not to copy somebody. That third Kris Kross album, Young, Rich & Dangerous, it don’t sound like nobody else’s records. And we were doing things that still were ahead of its time that people were even doing.”

Kris Kross split up following that album, and Smith and Kelly largely disappeared from the public eye. In later years, Smith started the fashion and lifestyle brand Urbane Muse, where he sells all kinds of clothing and accessories, as well as his latest album, 2023’s SMITH, Vol. 1.

Kelly spent his post-fame years studying audio engineering, operating his own indie record label, and running a daycare facility with his mother, according to The New York Times. He reportedly still wore his pants backward. Somewhere along the way, like so many teen stars before him, Kelly developed a drug habit. On May 1, 2013, he died of an overdose. He was just 34. 

“Our friendship began as little boys in first grade,” Smith said in a statement. “We grew up together. It was a blessing to achieve the success, travel the world and entertain Kris Kross fans all around the world with my best friend.”

Before Kelly’s untimely passing, Kris Kross performed one last time. The duo took the stage at Atlanta’s Fox Theater on February 23, 2013, at a concert celebrating the 20th anniversary of So So Def, the label founded by Jermaine Dupri. By this time—thanks partly to Kris Kross paving the way—Atlanta had become a hotbed for rap music. Their setlist included “Warm It Up,” “Jump,” and “Live and Die for Hip Hop.” 

In light of what happened less than three months later, Kelly’s opening lines on the first verse of “Live and Die for Hip Hop” seem to punctuate the entire Kris Kross saga. “I devoted my whole life to rockin’ mics, gettin’ crowds lifted,” Kelly rapped that night in Atlanta. “Put my pants on backwards ’cause I wanted to be different.”

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