When Jermaine Dupri discovered Chris Kelly and Chris Smith in 1990, he told the Times, "They reminded me of myself when I was younger. I didn't know what I was going to do with them, but I knew it would be something." And indeed it was. Soon after meeting, the trio produced a demo tape and not long after, Kelly and Smith signed their first contract with Ruffhouse Records (via Biography).
It didn't take long for them to taste success either with "Jump" debuting on February 6, 1992, the first single from Totally Krossed Out. It was a hit to say the least, spending eight weeks at No. 1 on the Billboard Hot 100. As AllMusic notes, the enormous success of "Jump" was part marketing savvy, too, with writer-producer Dupri not only sampling the Jackson 5's "I Want You Back," but also having Kris Kross wear their clothes backwards, which would become their signature. In explaining their style, Smith had said, "Kris Kross means up is down, left is right, and the inverse is the adverse" (per the Times).
But as many teen acts do, Kris Kross was unable to make a smooth transition past puberty. Their image of backwards-clothes-wearing teens was far too great to escape and they struggled with finding their voice. In an attempt to escape their teen image, Kelly and Smith tried to portray a tougher one, but fans were not as receptive. Four years after forming, and not yet 20, Kris Kross would part ways after the release of their third studio album Young, Rich and Dangerous.
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