After his father died when he was just eleven, Holiday was raised alone by his mother in Washington, D.C., and Alexandria, Virginia.

Holiday attended a local high school where he displayed his singing talent during a showcase night.

By then, he frequently listened to Marvin Gaye, Boyz II Men, Tupac Shakur, R. Kelly, and Jodeci.

Although he had the passion to go deep onto the music path, his mother wanted him to complete his education.

The single has also debuted on BET's 106 & Park countdown at number 9 on Tuesday July 31, 2007.

"It's Yours" was the first single from the album, which featured production from The Co-Stars (Teairra Mari's "Make Her Feel Good"), and Jasper Cameron (Lloyd's "Player's Prayer").

The song was well received, becoming the most added single at Urban Mainstream radio the week of December 13, 2008.

The second single that was supposed to be released was "Fall", but due to label problems it was canceled like "Come Here" on his previous album.

Holiday left Capitol Records and signed to Def Jam at the time working on his third album.

Holiday has been receiving heavy rotation of his single "Sign My Name" and has been on multiple radio stations giving the fans what they need.

His "Sign My Name" Tour has kept him busy to the point of have performance dates booked months in advance.

He embarked as the headliner in the "Bad Boyz of R&B" Tour and the release of the movie "School of HardKnocks" that he starred in alongside Elise Neal, Erica Hubbard and Cisco Reyes was highly anticipated.

[13] Guilty Conscience was pushed back again and was released on January 28, 2014, through his label Holiday Music Group.

On October 5, 2018, the lead single "25 to Life" was released, and an upcoming album entitled Time has been announced in the works.

[14] His 2019 single "Feel Like" was released, and has also announced his upcoming tour "Underrated Part I" which started in Birmingham, Alabama on August 3, 2019.