Born in Cambridge, Massachusetts, Ladd started his career in music in high school by playing bass or drums in a variety of garage bands. However, his roots lie in poetry and performance, with close ties to largely spoken-word artists like Saul Williams or Carl Hancock Rux as well as underground rap maestros like El-P or New Flesh.  

Ladd is the winner of the Nuyorican Poets Café Slam; his writing was also published in the 1996 protest tome In Defense of Mumia. He released his first album, Easy Listening 4 Armageddon, in 1997; its success led to a deal between his Likemadd label and Ozone Music for 2000's Welcome to the Afterfuture and the following year's Vernacular Homicide EP.

In 1998, Ladd recorded a single for top British underground label Big Dada, and he returned there for his third full-length album, 2000's Gun Hill Road. The first in a trilogy of underground full-length albums staging a battle between the forces of good and evil (in hip-hop), it was followed by the second in the trilogy, Beauty Party, in 2003. Ladd currently lives in France with his family.