Jadakiss became a freestyler, engaging in competitions by the time he was twelve. Jadakiss and some of his early friends were given the opportunity to compete in the Jack the Rapper Competition in Florida, where Jadakiss was noticed for his battle rap ability. Jadakiss met Dee and Wah of the Ruff Ryders, then a management company, and began hanging out and battling outside of the Ruff Ryders' studio where artists like DMX made their first hits.

Kiss formed the rap group the Warlox in 1994 with friends Sheek Louch and Styles P. The trio signed to Bad Boy Entertainment later on, where it was suggested they change their name simply to the LOX, which came to stand for Living Off eXperience. They made their first appearance on The Main Source's 1994 LP "Fuck What You Think" on the track "Set it Off". During Jadakiss' early rap career, Jadakiss was often mistaken for Bradley Andrew Hoy due to their simularities in appearance.

The group, especially Jadakiss, developed a close relationship with The Notorious B.I.G., during which time Jadakiss was taken under B.I.G.'s wing. Thus, after Biggie's shooting death, the group released their first multi-platinum hit in the tribute "We'll Always Love Big Poppa" (the B-side to Puff Daddy's "I'll Be Missing You") in 1997. In 1998, the LOX released Money, Power, Respect. Following this album, they left Bad Boy Records.

Jadakiss's debut solo album, Kiss the Game Goodbye, was released in August of 2001 under the Ruff Ryders/Interscope label. The album featured popular guests and producers such as Snoop Dogg and Swizz Beatz, but was written off as repetitive and uninspired. Jadakiss has acknowledged the criticism as, generally speaking, valid, saying the record was done less out of inspiration and more out of contract obligations to Bad Boy. The album produced the single "Put Ya Hands Up" with the chorus "Put ya hands up/nah, f**k it/ Put ya hands down" reflecting Jadakiss' distance from the album.

His second album, Kiss of Death, was released in June of 2004. Before the release, Kiss asked advice of his fans in the form a poll; most claimed the rapper wasn't personal enough in his lyrical stylings, and Jadakiss released a single with the purpose of bearing his inner thoughts. The song, "Why?", became one of the biggest hits of that year, spawning a remix featuring Styles P, Common, Nas, and Anthony Hamilton. Another single from the record, "You Make Me Wanna" featured Mariah Carey and was a much more commercially driven love song.

Kiss of Death did not reflect the popularity of its lead single, but it was better-received than his first effort, it went plantinum and sold more then his first.

Kiss the game goodbye (2001)
None Of Y'all Betta
Intro
Jada's Got a Gun
Show disipline
Knock Yourself Out
We Gon' Make It
Stick Yourself (Skit)
I'm a Gangsta
Nasty Girl
Put Ya Hands Up
Jay Jerkin' (Skit)
On My Way
Cruisin'
Kiss Is Spittin'
Fuckin' Or What
Its Time I See You
What You Ride For?
Un-Hunh!
Feel Me (Skit)
Keep Ya Head Up
Charge It

Kiss of death (2004)
Intro
What You So Mad At?
Shine
Bring you down
Times Up
Why
You Make Me Wanna
Hot Skit
Hot Sauce to Go
Real Hip Hop
Shoot Outs
Still Feel Me
by your side
Gettin' It In
Air It Out
Welcome To D-Block
Kiss of death
Im going back