2009–present: All or Nothing with Cash Money Records

On 15 October 2008 during the MOBO Awards, Jay Sean announced that he had signed with the American hip-hop oriented record label Cash Money Records distributed via Universal Republic Records making him the first British Asian singer to sign with an American label. His American-debut single was "Down" featuring American superstar rapper and label mate Lil Wayne, and topped the Billboard Hot 100 replacing Black Eyed Peas.

At the 2009 UK Asian Music Awards (AMA), Jay Sean won three awards, including "Best Male", "Best Urban Act" and "Best Album" for My Own Way. He met with Rishi Rich, Juggy D and H-Dhami during the ceremony.

On his first interview in America with MTV IGGY, Jay announced that he was recording five new songs for his then upcoming release of My Own Way (U.S. edition), one of which was his American-debut single with Lil Wayne, later titled "Down". Jay discussed a collaboration with Akon at the 2009 Grammy Awards, in addition to recording a song with Nadine Coyle and believes the album will be released in third quarter of 2009. However, the album title has now been confirmed to be All or Nothing and will feature brand new songs.

Jay Sean has also featured on a song called "Written On Her" alongside Birdman for the CEO’s next project, released on 23 June 2009 on iTunes. This song was played during an interview on Westwood Radio 1 with Birdman and Jay Sean. Jay Sean has featured on Skepta's single "Lush" released on 10 June 2009 on iTunes. He will also feature on Kevin Rudolf's single "Cash Money Heroes" with Birdman and Lil Wayne.

Jay Sean was in early September 2009 nominated for the 30 Under 30 award.

His single "Down":
    #1 Top
    #1 Pop Songs
    #1 Radio Songs
    #6 Digital Songs
    #7 Ringtones
    #3 Canadian Hot 1...