David's earliest exposure came when he worked on a b-side to British group Damage's song "Wonderful Tonight." He then started doing vocals for a few tracks with garage act Artful Dodger. The song "Rewind," released off the Artful Dodger album It's All About the Stragglers, hit #2 on the UK charts in 1999; thus, paving the way for a solo career. David's first single, "Fill Me In," made him the youngest solo male artist ever to reach #1 in the UK (he was 19 years old at the time). This was the first of a string of four Top 10 singles from his debut album Born To Do It, which eventually sold more than seven million units worldwide, earning multi-platinum status in more than 20 countries. The song "Key To My Heart," taken from the US version of the album, was also featured on the award-winning Warner Brothers animated film Osmosis Jones.The success of David's debut, which was written almost entirely by David and Mark Hill of Artful Dodger, led to the U.S. release of "Fill Me In" in May 2001. It reached #15 on the Billboard Hot 100. Born to Do It was released in the U.S. on 17 July 2001, peaking at #11 on the Billboard 200 and sold over one million copies. The single "7 Days" hit the Top 10 in the U.S.; although, "Walking Away," which had reached #3 in the UK and #5 in Australia, missed the Top 40 in the U.S. and was the last of his singles to chart there.

In April 2009, MTV viewers voted 'Born To Do It' as #2 on their 'Greatest Album of All-Time' poll.

The follow-up album, Slicker Than Your Average, was released in 2002 and fared considerably less well than David's debut. None of the six singles released from the album charted in the U.S. Although "What's Your Flava?" and "Rise & Fall" (duet with Sting) received airplay on the Urban contemporary and Soft AC formats, they did not make the Hot R&B/Hip-Hop Singles Tracks chart or the Adult Contemporary chart. However, "What's Your Flava?" made the Rhythmic Top 40 (#32), Top 40 Mainstream (#24) and the Top 40 Tracks (#37). The albums' first four singles continued his streak of Top 10 hits in the UK, bringing a total of nine consecutive Top 10 hits until "World Filled with Love" peaked at #15 in 2003. According to the RIAA Slicker Than Your Average reached Gold Status in the USA.

David later signed on with Warner Music and put together his third album, The Story Goes..., which was released worldwide in August 2005 (excluding the U.S. where it was never released). The first single, "All The Way," returned him to the Top 3. The second single, "Don't Love You No More (I'm Sorry)," tied with "7 Days" as his longest running single in the charts since "Rewind," spending 15 weeks inside the UK Top 75. The album's third single, "Unbelievable," debuted at #18 in March 2006.

In 2007, David collaborated with UK rapper Kano on his upcoming album London Town, for the single "This is the Girl." The track was released on 27 August 2007 and debuted at #18 on the UK charts.

The first single "Hot Stuff" from the album Trust Me, was released on 5 November 2007 . The single was a top ten hit, whilst the album charted at #18 on the UK Albums Chart. "6 of 1 Thing," the second single to be taken from Trust Me, charted at #39 on the UK Singles Chart, becoming his third-lowest charting single to date.

"Officially Yours" was released on 23 June 2008 and peaked at #158 on the UK Singles Chart, becoming his lowest-charting single to date and was the final single from Trust Me.

In July, a new track titled "Are You Up For This" started receiving airplay on various radio stations as part of a promo with Ice Cream Records, which also featured a remix with Witty Boy.

On 17 August, David performed at a birthday tribute concert for songwriter Don Black at the London Palladium. He performed the song "Ben," originally a hit for Michael Jackson.

David took part in Soccer Aid 2008 at Wembley Stadium on 7 September 2008. He picked up the 'Man of The Match' award on the night and played in the same England side as ex-internationals such as Alan Shearer, Teddy Sheringham and David Seaman, and played against the likes of Romario, Paolo Di Canio, Jaap Stam and Luis Figo.

David received two 2008 UK Urban Music Award nominations for Best Album with Trust Me and Best R&B Act.

On 7 November, David was recognised for his contribution to the music industry by receiving an honorary degree of Doctor of Music, from Southampton Solent University at a graduation ceremony held at Southampton Guildhall.

On 29 December, a new mix of "Insomnia," titled "Up All Night Mix," was made available for digital download.