“Lawnge:…everybody said he looked like Dres so that was the association. Everyone kinda really forced that relationship like is that Dres’ little brother? It was like no but we know him. That’s how we really connected.
Dres: There’s a lot of love though.”
Chi first made his first appearance as ‘Jeff’ on various B-Sides to singles from De La Soul’s 3 Feet High and Rising. He soon reappeared as Chi Ali two years later on Black Sheep’s debut album A Wolf In Sheep’s Clothing on “Pass the 40”, a posse cut about drinking 40s, rocking the ladies, and the mic. Chi Ali at the time was a member of the Native Tongues family and also had connections with the Legion family, along with Showbiz and A.G.
Soon after “Pass The 40,” Chi released his first solo single “Age Ain’t Nothing But a #”. The song was a moderate hit. It was popular on urban radio stations, and the video got good rotation on Yo! MTV Raps and Rap City. The album in which the song was featured was released shortly thereafter yielding a couple other singles, “Roadrunner” and “Funky Lemonade,” which were both remixed and rerecorded, making them different than their album versions. They featured Chi with a slightly more mature voice. Overall, the album’s theme is of a kid who is getting too big for his britches. He speaks of preferring to date older women, gun toting, and marijuana smoking, which at the time seemed cute and laughable. It received mixed reviews for lyrics that seemed uneven, overall excellent production, and for Chi being outclassed by his Native Tongue associates.
Chi Ali seemingly disappeared from the rap world until the late 90’s when he appeared on Dres’ solo album Sure Shot Redemption. Chi’s demeanor was no longer that of a carefree mischievous child, but of an angry, thug-like individual. The album got little press and mixed, though overall good reviews.
Shockingly, the next time many would see Chi Ali was on the show America’s Most Wanted in 2001 for the death of Sean Raymond, the brother of his then girlfriend. Chi evaded police for a number of weeks before his capture by a now retired detective. Reports at the time indicated that the incident stemmed from the loss of $300 and an unknown number of CDs. Chi Ali is currently serving a 14 year sentence at Elmira Correctional Facility, in Elmira, NY.
In 2006, Chi was featured in a segment of the E! Entertainment television show Child Star Confidential on the episode titled Famous Little Faces. In the show, Chi explained what triggered the confrontation with Raymond. He said that his girlfriend, from whom he was estranged at the time, called him to ask for money for their child. He said he then spoke with Raymond, who was with his sister, and asked him to give her $20. According to Chi, Raymond told him to “suck my dick.” Chi became very angry, went over to the apartment where his girlfriend and her brother were, got into an argument with Raymond, and then shot him. On the TV show, Chi said, “I was very upset that night. Thirty seconds, man, can change your whole life. And, you know, I’m paying for it.”