Following the 1998 release of his album I've Been Expecting You, and in the middle of promotion and touring in 1999, Williams found time to start the work on what would be his third studio album.
The sound of the album was described as seeing Williams move "farther away from the increasingly dated visions of Oasis-style Britpop to embrace post-millennial dance-pop, complete with the bruising beats and extroverted productions to match." The album features a variety of styles, "conjuring a panoply of classic British rock touchstones like psychedelia, slick country rock, Ian Dury, the Who, Elton John, and Madchester."
Initial releases do not feature Williams' name or the album title on the front cover, no track listing featured on the back cover; these were all changed for future releases. The images were taken by photographer Paul M. Smith and, along with Williams' complete football strip, were later sold at auction to raise money for his charity Give It Sum. Williams toured the United Kingdom with Kylie Minogue in October and November 2000 to promote the album, selling out in every venue.
The album contains a hidden message put on the album for humorous intent. After 24 minutes of silence following track 12, "The Road to Mandalay" (4:08 - 28:08), a spoken message from Williams saying "No, I'm not doing one on this album" is heard, which means that no hidden track on the album. This is a reference to how Williams' past three albums (including the compilation album The Ego Has Landed) each contain hidden tracks at the end of the album.
When the album was released on 28 August 2000, it immediately became a hit in the United Kingdom, debuting at number-one and being certified 2× Platinum in the first week of release. The album also topped the charts in New Zealand, Ireland and Germany, and secured top ten placings in Argentina, Austria, Australia, Finland, Mexico, Sweden, Switzerland. Sing When You're Winning failed to reach the top 20 in Spain, reaching number 22. The album spent 91 weeks on the UK chart, going on to sell 2.4 million copies in the UK alone, being certified 8× Platinum by the BPI. The album became the best-selling album of 2000 in the UK, and the 51st-best-selling album in UK music history. The album found little success in the United States, however, peaking at 110 in the Billboard 200.
Initial critical response to Sing When You're Winning was positive. From Metacritic, which assigns a normalised rating out of 100 to reviews from mainstream critics, the album received an average score of 69, based on 11 reviews.
"Rock DJ" was released as the album's first single. The song was inspired by Williams' UNICEF mentor, the late Ian Dury. The video was censored by Top of the Pops for its gore content, with many other channels following suit. Controversy ensued in the United Kingdom and many other countries, with the video showing Williams tearing chunks of skin and muscle from his body while performing a strip show, in an attempt to get noticed by a group of women. The track became an instant hit around the globe, hitting number one in the United Kingdom, becoming his third number-one single as a solo artist and exactly a year after his sell-out concert at Slane Castle. The song also reached number-one in Ireland, New Zealand, Mexico and Argentina and hit top-ten placings across Europe, Australasia and Latin America. Despite its worldwide success the song failed to break into the United States charts, although it did get some TV airplay on MTV and VH1. The song went on to win several awards including "Best Song of 2000" at the MTV Europe Music Awards, "Best Single of the Year" at the Brit Awards and an MTV Video Music Award for Best Special Effects. It went on to sell over 600,000 copies in the UK alone, and was certified Platinum by the BPI.
"Kids", a collaboration with Australian pop icon Kylie Minogue, was released as the album's second single. The track was written when Minogue approached Williams to write some songs for her debut Parlophone album Light Years. Williams decided to include the track on his album and released it as a single, becoming an instant hit upon release in October of that year. The song hit number two in the United Kingdom and snared top 10 placings in Australia, New Zealand, Latvia, Mexico and several other countries. One of the biggest hits of 2000, "Kids" sold over 200,000 copies in the UK alone and was certified Silver.
"Supreme" was released as the album's third single, and was promoted in various countries by several international-language versions, including versions of the song in French and Spanish.
"Let Love Be Your Energy" was released as the album's fourth single, and was the first Robbie Williams music video not to feature Williams himself. Instead, the video was animated and featured Williams attempting to outrun a volcano.
"Eternity", a track that was not featured on the album, was released in the summer of 2001 backed with "The Road to Mandalay", a song which appears as the final track from the album. "Eternity" was written by Williams in what he called "the most amazing summer ever". After years of non-stop work he took a month off and recorded this track, which became his fourth number-one single in the United Kingdom, selling over 70,000 copies in its first week. It also became a top ten hit all over Europe.
"Better Man" was released as the album's sixth and final single, exclusively in Australia and New Zealand. The single was released to relative success there.