By the age of 16, Jadakiss was a freestyle rapper. He and some of his friends were given the opportunity to compete in the "Jack the Rapper Competition" in Florida, where Jadakiss had been noticed for his battle rap ability. He 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 such as DMX made their first hits.
Jason Phillips founded the rap group The Warlocks in 1994 with friends, Sheek Louch and Styles P. They later signed to Bad Boy Entertainment, where it was suggested that 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."
The group, especially Jadakiss, developed a close relationship with The Notorious B.I.G., during which time Jadakiss was taken under Biggie's wing. The LOX's first hit was the tribute to The Notorious B.I.G. called "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. Though the record was successful, eventually going Platinum, The LOX grew unhappy with Bad Boy Records and Puffy's glossy, radio friendly production. Following this album, they left the label to sign with Ruff Ryders Entertainment.
2001-2003: Kiss Tha Game Goodbye
Jadakiss's debut album, Kiss Tha Game Goodbye, was released in August 2001 on the Ruff Ryders/Interscope label. The album featured popular guests and producers such as DJ Premier, The Alchemist, DMX, 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 than out of contract obligations to Bad Boy. The album produced the single "Put Ya Hands Up."
Jadakiss is mentioned in Eminem's 2002 song 'Till I Collapse as one of the best rappers in the industry.
2004-2008: Kiss of Death and signing to Def Jam
Jadakiss's second album, Kiss of Death, was released in June 2004. His song "Why?" (featuring Anthony Hamilton) became one of the year's biggest hits, spawning a remix featuring Styles P, Common, Nas, and Hamilton. "Why?" remains Jada's biggest hit, peaking at #11 on the Hot 100. Another single from the record, "U 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.
In late 2007, Jadakiss signed to Jay-Z's Roc-A-Fella Records, a move Jay had been trying to arrange for a long time. The move came on the heels of increased D-Block/Roc-a-Fella collaborations; in 2006, Jadakiss and former rival Beanie Sigel collaborated on DJ Khaled's album Listen...the Album, and in 2007, on Freeway's album Free At Last. Styles P appeared on a radio freestyle with Freeway and Sigel, and also appeared briefly in the video for Jay-Z's American Gangster single "Roc Boys," in which he throws up the famous Roc-a-Fella sign, "the Diamond."
2009-present: The Last Kiss, and Top 5, Dead or Alive
In 2009, Jadakiss released his third official album, The Last Kiss. The first single is "By My Side", featuring Ne-Yo. The second official single is "Can't Stop Me". The third official single is "Death Wish", featuring Lil Wayne. The fourth official single is "Who's Real", featuring Swizz Beatz and OJ Da Juiceman. In 2010, Jadakiss reunited with the Ruff Ryders label while remaining at Roc-a-Fella.
In 2011, he was featured on two DJ Khaled tracks, one of them titled "It Ain't Over Til It's Over", also featuring Mary J. Blige and Fabolous, and "Welcome to My Hood (Remix)," also featuring Ludacris, Busta Rhymes, Twista, Mavado, Birdman, Ace Hood, Fat Joe, Game, Bun B and Waka Flocka Flame. On April 26, 2012, Jadakiss released his mixtape Consignment.
On June 4, 2013 Jadakiss released the first single from his upcoming fourth studio album Top 5, Dead or Alive titled "Big Boy Dialogue" featuring vocals from The-Dream. The album will feature guest appearances by The Lox, Young Jeezy, Wiz Khalifa, Chris Brown, Rick Ross, and Lil Wayne. He also announced that a collaboration mixtape with Yo Gotti would be released prior to the album. The album is scheduled to be released during September or October 2013.