May 1 marks the third anniversary of the death of  Chris “Mac Daddy” Kelly. One half of Kris Kross, Mac Daddy had skyrocketed as one of the 1990s’ biggest Rap acts. He (with partner Daddy Mac) would reach the mainstream with multiple hits, appear in music videos with Michael Jackson, and even release a video game for the Sega Genesis console. By the 2010s however, the Atlanta, Georgia native personally battled drug addiction, a challenge that would eventually cost him his life.

In looking back at Kris Kross’ legacy, it can often veer solely towards seminal RuffHouse/Columbia Records hits like #1 chart topper “Jump” and “Da Bomb.” However, history cannot overlook the fact that of the three albums Kris Kross released, all three achieved gold or platinum-plus status. Unlike so many artists lumped in the “kiddie Rap” sub-category, Kris Kross exited the game as all-stars. 1996’s final LP, Young Rich & Dangerous would release in the first month of a year that witnessed game-changing albums by Tupac Shakur, Jay Z, Nas, and label-mates The Fugees. The guard, sound, and style was changing in Rap, and perhaps big antics, beef, and mafioso themes eclipsed some of the first ATL Rap stars ever on the scene.

Jermaine Dupri Discusses His Role With Kris Kross, TLC, & Fresh Fest ’84 (Audio)

Still, the numbers do not lie. Young, Rich & Dangerous would go gold (within two months), and debut at #15 on the charts. In their upper teens, Mac Daddy and Daddy Mac were basking in their track record of commercial success—just as ‘Pac, Wyclef Jean, and Jay Z would later do. The album featured one of their own proteges in Da Brat, who had now solidified a strong solo career, as well as Aaliyah. Jermaine Dupri, Kris Kross’ mentor, remained at the helm of the LP’s sounds. There, he proved himself as a pop-savvy sampler, on the cusp of mass appeal through “So So Def” production for Usher, Mariah Carey, and Monica.

1995 set-up single “Tonite’s Tha Night” would be one of Kris Kross’ final chart-worthy hits (#1 on Rap charts, #12 overall). Produced by J.D., the gold-certified song used Faze-O’s cool-out classic “Ridin’ High” to give the two Chris’s a vastly different aesthetic than Heads knew them for in their younger days. These were smooth-talking upper-teens feeling their pockets, charms to the females, and linguistic abilities. The track was also a nod to EPMD’s six-year-old jam, “Please Listen To My Demo,” indicated by slickly recruiting Def Squad member Redman for the video remix.

For the original video, multiplicity was the theme. The group showed their many sides, which was a theme on that third LP. Just as was heard upon their introduction, the duo was showing their influences by the likes of West Coast Hip-Hop stars such as Eazy-E, DJ Quik, and contemporary Snoop Dogg.

Despite the trimmings of success in 1996, Kris Kross would leave RuffHouse/Columbia with one its executives, Joe “The Butcher” Nicolo. Although Mac Daddy and Daddy Mac recorded, they never released the correlating album. The group remained in tact though, performing at the So So Def 20th Anniversary concert, just weeks prior to Kelly’s death.

Ambrosia For Heads’ Do Remember Features.

#BonusBeat: The “Tonite’s Tha Night (Remix)” featuring Redman:

Related: DJ Wonder – Kris Kross Tribute Mix