How Kriss Kross Pioneered the Backward Fashion Craze

In the music industry, a striking image and a clever hook can propel you to stardom, but pair that with an unforgettable track—one that people can still sing along to decades later—and you’ve unlocked the formula for extraordinary success. This is precisely what Kris Kross, the teenage rap sensation of the ’90s, achieved during their meteoric rise.

Kris Kross, comprising Chris “Mac Daddy” Kelly and Chris “Daddy Mac” Smith, burst onto the global stage with their 1992 smash hit, “Jump.” The track soared to the top of the Billboard Hot 100 in just four weeks, driving their debut album, Totally Krossed Out, to the pinnacle of the Billboard 200. Within a year, the album achieved quadruple platinum status.

“Jump” was an irresistibly catchy anthem, crafted from samples of iconic tracks like The Jackson 5’s “I Want You Back.” When the chorus hit with its energetic “Jump! Jump!” refrain, it was nearly impossible to stay still. Adding to their appeal was their signature style: Smith and Kelly donned oversized sports jerseys, baggy jeans, and baseball caps—all worn backward, creating a trend that captivated fans worldwide.

Kris Kross proved they were more than just a one-hit wonder. Their sophomore album, 1993’s Da Bomb, achieved platinum status, and their third and final release, 1996’s Young, Rich & Dangerous, went gold, delivering one last Top 20 hit with “Tonite’s Tha Night.” However, shifting musical trends and the inevitable evolution of artists’ careers meant their time in the spotlight was short-lived. 

When Chris Kelly passed away from a drug overdose on May 1, 2013, at 34, it had been years since Kris Kross was a household name. Yet, his death instantly sparked a wave of nostalgia among millions in their thirties, who fondly remembered the days when Mac Daddy and Daddy Mac had everyone jumping. 

Origins in the Mall

Chris Kelly and Chris Smith first met as first graders in Atlanta. “We’re like twins who don’t resemble each other,” Smith explained to The New York Times in 1992. Bonding over their shared passion for hip-hop, they would rap along to tracks by Eric B & Rakim and Run-DMC. Though they dreamed of showbiz, it seemed out of reach—until a chance encounter at Greenbriar Mall, where they saw the local rap group Silk Tymes Leather while shopping for sneakers.

Smith and Kelly approached the group for an autograph, catching the attention of their producer, Jermaine Dupri, a driven music industry professional whose father had managed tours for acts like the S.O.S. Band and Cameo. Dupri noticed how everyone in the mall seemed captivated by the sharply dressed preteens, as if they were already stars.

“I’d never seen kids who looked like me,” Dupri shared with The Washington Post. “That’s what stood out. They were dressed even sharper than me—almost. Brand-new sneakers. I thought, ‘Hold on. How old are these two?’”

Dupri took down the boys’ contact information, even though they admitted they didn’t rap seriously and only danced occasionally. He saw their potential and spent the next few years honing their rapping skills. According to Dupri, their abilities “transformed from awful to outstanding,” and by spring 1991, he secured them a contract with Ruffhouse Records, a label under Columbia’s distribution. 

Joe Nicolo, the head of Ruffhouse, was reportedly struck by “Lil’ Boys In Da Hood,” a track that delved into the challenges of urban life through the eyes of two young, clean-cut rappers who conveyed their message without using profanity.

Totally Krossed Out

Jermaine Dupri was the creative force behind nearly every track on the duo’s debut album, Totally Krossed Out. While the project took roughly two years to complete, he revealed that “Jump,” the track that catapulted Kris Kross to worldwide fame, was crafted in just 30 minutes.

“The goal was to create a call-and-response anthem that everyone could join in on,” Dupri explained to Complex in 2013. “Since they were kids, I knew it needed a hook to resonate. The concept came from observing crowds at concerts—everyone was jumping, so I thought, why not make a song about that?”

The final touch was their unique fashion sense. Kelly and Smith mentioned in interviews that they collaborated with Dupri to perfect their backward-style aesthetic, which they dubbed the “totally krossed out” look. (Angela Smith, Chris’s mom, shared with The Washington Post that she coined the duo’s name, inspired by a teacher who nicknamed Kelly “Chrissy Crossy Apple Saucy” due to his love for applesauce.)

“Kris Kross represents flipping the script—up becomes down, left turns right, and opposites attract,” Smith stated in The New York Times. “That’s our identity. That’s why we wear our clothes backward.”

The duo’s iconic style was showcased on March 29, 1992, when Kris Kross performed their hit “Jump” on the popular Fox sketch comedy show In Living Color. Though the single had been released in February without much initial buzz, their prime-time TV appearance propelled it to debut at No. 61 on the Billboard Hot 100, skyrocketing to No. 12 the next week. By April 25, it claimed the top spot as America’s No. 1 song.

Even critics couldn’t resist. Robert Christgau, often referred to as the “Dean of American Rock Critics,” lauded “Jump,” describing it as “a masterpiece that reminds us why rock and roll matters, a seemingly simple track that transcends deeper questions of meaning and authenticity.” The song also secured third place on The Village Voice’s esteemed Pazz & Jop year-end critics poll.

“Jump” dominated the charts for eight consecutive weeks, during which Totally Krossed Out reached the pinnacle of the Billboard 200 album chart for two nonconsecutive weeks. The album spawned another Top 20 hit with “Warm It Up,” and in June 1992, Kris Kross made a cameo in Michael Jackson’s “Jam” music video. That summer, they joined Jackson as special guests on the European leg of his Dangerous World Tour.

A Side of Beef

A lesser-known aspect of Kris Kross’s rise was their involvement in a four-way rivalry with Atlanta’s Another Bad Creation (ABC), Philadelphia’s Da Youngsta’s, and the duo Illegal, which included Snoop Dogg’s cousin, Mr. Malik. In the opening lines of “Jump,” Kelly raps, “Don’t try to compare us to another bad little fad,” a direct dig at ABC. 

In April 1993, Da Youngsta’s entered the feud with their track “Crewz Pop,” which included a diss aimed at Kris Kross: “I pray for the chump that bumps me or plays me like a punk / So jump, jump if you want me.”

Kris Kross retaliated in August 1993 with “Alright,” where Smith rapped, “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 1992 single by Da Youngsta’s.) That same year, Illegal released “We Getz Busy,” with Mr. Malik calling out Kris Kross by name and criticizing them for using lyrics they didn’t write: “Can’t write ya own rhymes, sellin’ Jermaine’s life stories.” 

Malik later revealed in 4080 magazine that he and his bandmate, Jamal Phillips, got into a physical altercation with Kris Kross at MTV’s Ed Lover’s birthday party. Despite the clash, Kris Kross continued their career, while the other groups gradually faded into obscurity. 

Jumping Back to Earth

Rap stardom in the ’90s was often short-lived (think MC Hammer and Vanilla Ice), but Kris Kross defied expectations by staying relevant longer than many anticipated. Their 1993 sophomore album, Da Bomb, embraced the West Coast hip-hop vibe popularized by Dr. Dre, delivering a more mature sound. The single “Alright,” featuring Jamaican dancehall star Super Cat, broke into the Top 20 on the Billboard Hot 100, and the album achieved platinum status. 

The duo released their third album, 1996’s Young, Rich & Dangerous, which included the hit single “Tonite’s Tha Night,” peaking at No. 12 on the Hot 100—their highest chart position since “Jump.” The album also featured Aaliyah on the track “Live and Die for Hip Hop.” Although it only achieved gold status, Jermaine Dupri later praised the project in an interview with okayplayer.

“That album is filled with hood-classic tracks,” Dupri remarked. “When we create music, we always aim to be original. Young, Rich & Dangerous doesn’t sound like anyone else’s work. We were doing things that were ahead of their time, setting trends others would follow.”

After the album’s release, Kris Kross disbanded, and Smith and Kelly stepped away from the spotlight. Years later, Smith launched the fashion and lifestyle brand Urbane Muse, offering a range of clothing, accessories, and his 2023 album, SMITH, Vol. 1.

Kelly pursued audio engineering, managed his independent record label, and co-ran a daycare center with his mother, as reported by The New York Times. He was known to still wear his pants backward. Sadly, like many former teen stars, Kelly struggled with addiction and passed away from an overdose on May 1, 2013, at the age of 34. 

“Our friendship started in first grade as little boys,” Smith stated in a heartfelt message. “We grew up together and were blessed to achieve success, travel the world, and entertain Kris Kross fans everywhere with my best friend.”

Just before Kelly’s tragic death, Kris Kross reunited for a final performance. On February 23, 2013, the duo graced the stage at Atlanta’s Fox Theater during a concert marking the 20th anniversary of So So Def, Jermaine Dupri’s record label. By then, Atlanta had emerged as a rap music powerhouse, partly due to Kris Kross’s influence. Their performance featured hits like “Warm It Up,” “Jump,” and “Live and Die for Hip Hop.” 

Reflecting on the events that unfolded less than three months later, Kelly’s opening lines in “Live and Die for Hip Hop” take on a poignant significance. “I gave my life to rockin’ mics and lifting crowds,” Kelly rapped that night in Atlanta. “I wore my pants backward ’cause I wanted to stand out.”