He released his debut album, Back of My Lac’, in October 2007. The album debuted on the U.S. Billboard 200 chart at number 5 selling 105,000 copies in its first week. It debuted at #1 on the Top R&B/Hip-Hop Albums. The album debuted in the Top 20 R&B/Hip Hop albums in Canada and charted within the Top 100 albums in Canada. It became a Top 10 R&B/Hip Hop album in the UK and a Top 40 UK album entry peaking at #32. In the U.S. it also made it to #8 on the Tastemakers chart and #5 on the Top Digital Albums and Billboard Comprehensive Albums Chart. The lead single from this album was “Be with Me”, which stalled at #83 on the Hot R&B/Hip-Hop Songs Chart. Debuted on the U.S. Billboard Hot 100 in the issue week of July 4, 2007, at number 89 and has peaked at number 5. It was number 1 on the Hot R&B/Hip-Hop Songs for five weeks in a row. The single has also debuted on BET’s 106 & Park countdown at number 9 on Tuesday July 31, 2007. On Wednesday, August 15, 2007, “Bed” hit number one on its 11th day on the countdown. J. Holiday also performed “Bed” on 106 & Park on August 17, 2007. “Bed” was also performed on Showtime at the Apollo along with the single “Suffocate”. This song was #70 on Rolling Stone’s list of the 100 Best Songs of 2007. The video for “Bed” was ranked the #11 video of 2007 on BET: Notarized. His video for the third single, “Suffocate,” debuted on BET’s 106 & Park on November 7, 2007. The video was shot in Paris, France. “Come Here” was released as a single but was ultimately canceled.

Round 2 is the second studio album by Contemporary R&B singer J. Holiday. The album was released on March 10, 2009. The album is the follow-up to his gold-selling debut album Back of My Lac’. The album sold 55,000 units in its first week and debuted at number 4 on the Billboard 200. “It’s Yours” is the first single from singer J. Holiday’s second studio album, Round 2. The single features 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. Its Yours peaked at 25 on the US R&B chart. 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.

In 2010, J. Holiday left Capitol Records and signed to Def Jam at the time working on his third album. He then released his mixtape, M.I.A: The Lost Pages, in 2011, in promotion of the album. In early 2012, J. Holiday left Def Jam Recordings. On May 29, 2012, he released his single “Sign My Name”, from his upcoming third studio album. J. 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 embark as the headliner in the upcoming “Bad Boyz of R&B” Tour and the release of the movie “School of HardKnocks” that he is starring in alongside Elise Neal, Erica Hubbard and Cisco Reyes is highly anticipated. In July 2013, he revealed the title of his third studio album, titled Guilty Conscience, via Facebook. The album was scheduled to be released on November 11, 2013. He announced the lead single for the album titled “After We Fuck”, will be sent to urban radio soon. The album was pushed back until December 10, 2013. A music video for the single will be released on November 5, 2013. Guilty Conscience was pushed back again and was released on January 28, 2014 through his label Holiday Music Group. The album achieved #42 on Top R&B/Hip-Hop Albums.

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