Lif began the usual path for an independent rap artist: long nights spent honing his craft in the studio as well as testing his skill at open-mic sessions. He self-produced his first few independent records ("Elektro", "The Nothing", "Inhuman Capabilities", "Farmhand") while guest spots on notable peers' records like Jedi Mind Tricks' Violent By Design and collaborations with fellow Bostonians such as Akrobatik and 7L & Esoteric further solidified Lif's foothold in the underground movement. Lif made his first significant impact on the local airwaves with his song "Madness in a Cup" which was released by Boston based "Brick Records". Always thinking nationally and globally, Lif kept his targets set on working with a diverse but small collection of labels to project his sound. After working with The Beastie Boys' label "Grand Royal", he struck gold when he handed his debut EP "Enters the Colossus" (2000) to Definitive Jux CEO El-P (of Company Flow) just a couple months after the label was formed.

El-P and Mr. Lif formed a powerful alliance, which resulted in several successful collaborations. The era yielded some of Lif's landmark releases such as "Emergency Rations"(2002) (an EP that posed many radical thoughts to a post 9-11 America) and "I Phantom" (2002) (Lif's long awaited debut album) which provided a unique and poignant commentary on the American society by following a single character through many phases of life.

Regarded as a classic by many, "I Phantom" garnered the attention of mainstream music outlets like Rolling Stone and Spin. Soon other major Hip Hop publications such as XXL and The Source were catching on to this new breed of MC and hailing him for his innate ability and inimitable style. Lif and label mate Aesop Rock joined forces to tour from 2003 - 2004 before Lif took a break from the road to collaborate with long time friends Akrobatik and DJ Fakts One. The three formed their group "The Perceptionists", and the effort yielded the critically acclaimed "Black Dialogue" album released by Definitive Jux in 2005. "Black Dialogue" was the only independent rap album to appear on Rolling Stone Magazine's Top 50 records of 2005 list.

A rigorous tour schedule came along with the album's success, but after a year, Lif again left the road to return to the studio. He reunited with long time friend El-P in order to craft his second solo album, and their work resulted in the "Mo' Mega" album (2006 Definitive Jux). Once again, a "Mr. Lif" project received critical acclaim. However, unfortunately on Dec 2nd 2006, while touring to support "Mo' Mega," the life of this consistently rising star almost ended in a tragic tour bus wreck. The driver fell asleep at the wheel and dropped the bus 40 feet into a boulder-laden ravine. The bus caught fire, but amazingly everyone escaped before being engulfed in flames.

This was a pivotal moment in Lif's life and career. Though he had several contract negotiations with Definitive Jux, he declined to re-sign with his former label and chose to remove himself largely from the world of entertainment. During the most challenging moments of his reclusion, Lif penned a collection of songs describing not only the near fatal bus wreck, but the often torturous and disorienting months and years that followed.

In 2010 he recorded “Sak Pase” with The Perceptionists, a moving portrait of the earthquake that struck Haiti that winter. Lif also created his own NFL talk show “Big Games with J. Haynes.” The series covers not only football but music as well. According to Lif, the show “is my way of bridging the gap between my loves for hip hop and football. Listen and you'll hear high energy comedic sports talk over vintage hip hop beats.”

In December Lif played the Seattle Folk Festival with The Brass Menazeri. They immediately saw the opportunity to do something unique. Collaborating with the Brass Menazeri is bringing a fresh new sound to Mr. Lif’s work.