Richard Andrew was born in Yonkers, New York. With a mother who decorated the walls with records, and a father who played the guitar, Andrew was surrounded by music his entire life. Growing up, his family moved from apartment to apartment, which never gave him a real sense of home. He turned to music to offer him solace and a sense of home. At the age of 9, his father gave him a guitar, and although he did not have much interest in playing the guitar, it sparked his interest in becoming a musician. He found his passion in singing and rap, and began writing rhymes and singing around age 10.
Outasight began playing shows at small venues in New York City such as the Bowery Poetry Club and the Nuyorican Cafe. After his first EP release Employee of the Year, he played at the 2007 Hip-hop festival alongside major label acts such as Ghostface Killah, Skills, and Consequence. In June 2008, Outasight released his second promotional CD, titled Radio New York. This release saw more commercial success, and was featured in XXL Magazine's Soundcheck choice in "Something to Talk About." His music video for the song "Good Evening (Dream Big)" received a video rotation spot on mtvU in the Fall of 2008, after winning the 2008 mtvU Freshmen video contest. "Good Evening" was also popularized by its use in Ray William Johnson's Youtube-based vlog series: Breaking NYC.
In October 2009, Outasight signed with Warner Bros. Records. In December 2009, Lifted Research Group, better known as LRG, sponsored the release of Outasight's Further mixtape. His biggest release to date, Further has generated even more press than the previous two albums. The album was heavily publicized on the internet, garnering strong reviews and also promotion from YouTube celebrity Ray William Johnson. Since then, he has been featured in major media outlets, such as MTV News. On March 23, 2010, Outasight released the Further EP on Asylum Records, and plans to release his first full length studio album, sometime in 2011. Outasight released a music video for his single "Catch Me If You Can" from the Further EP, which has been featured on numerous hip-hop blogs. Also in 2010, Outasight collaborated with rapper Asher Roth on the "Catch Me If You Can" remix.