Outasight began playing shows at small venues in New York City such as the Bowery Poetry Club and the Nuyorican Café.

After his first EP release titled Employee of the Year, he played at the 2007 Hip-hop festival alongside major label acts such as Ghostface Killah, Skillz, and Consequence.

[6] "Good Evening" was also popularized by its use in Ray William Johnson's YouTube-based vlog series Breaking NYC.

The album was heavily publicized on the internet, garnering strong reviews and also promotion from YouTube celebrity Ray William Johnson.

[13] The commercial includes footage of Michael Jackson, Britney Spears, Mariah Carey, Ray Charles, and Kanye West.

Outasight performed live at the 2012 NHL All-Star Game in Ottawa, Ontario, where his single "Tonight Is the Night" was the song for the player introductions.

[2] Its lead single "The Wild Life" was released on July 29, 2015[17] and featured in the Bud Light Lime & Mountain Dew summer campaigns and several films.

[18][19] His next single, "The Boogie" was selected to be in the "Apple Watch 2" campaign, the opening introduction to the NBA Primetime on ABC, and also the credit song to the box office blockbuster Central Intelligence.

The song was featured in the film (Mike and Dave Need Wedding Dates) along with (The Nut Job 2: Nutty by Nature), (The Secret Life of Pets 2) and the soundtrack to the video game Madden 17.

"[28] On August 14, 2018, he announced his fourth studio album, Future Vintage Soul, with a scheduled release date of October 19, 2018.