Williams' renaissance continued with "Millennium" entering the UK singles chart at number 1 in September 1998, and I've Been Expecting You topping the album chart two months later. Williams was also announced to be the biggest selling album artist of 1998. Featuring backing vocals by Neil Tennant (Pet Shop Boys) and Neil Hannon (Divine Comedy), "No Regrets', one of Williams" finest songs to date, surprisingly stalled at number 4 in December. The wonderfully self-deprecating "Strong" debuted at the same position in March.
In 1999, Williams set about trying to woo America, touring in support of The Ego Has Landed , a selection of the best tracks from both albums. In November, he returned to the top of the UK charts with the double a-side, "She's The One"/"It's Only Us'. The former song was written and previously recorded by Karl Wallinger of World Party, ironic considering Williams' songwriting partner Guy Chambers was a former member of that band. The first airing of new material came in August 2000 with the release of Williams" third UK chart-topper, "Rock DJ", which was promoted by a controversial but award-winning video featuring the singer tearing lumps of flesh from his body. Sing When You're Winning proved beyond all doubt that Williams had won over the UK tabloids, music press and record buying public. Rarely has a dark horse enjoyed such a sweet victory. Of more dubious musical value was the Frank Sinatra-worshipping Swing When You're Winning , which included a beyond-the-grave duet with ole blue eyes himself on "It Was A Very Good Year" and an entertaining collaboration with actress Nicole Kidman on "Somethin' Stupid". Nevertheless, the album was another huge bestseller, and Williams was able to fulfill a lifetime's dream by appearing in a one man showcase at London's Royal Albert Hall.
In October 2002, Williams signed a record-breaking 80 million ($125m US) contract with his label, EMI Records . The contract featured a number of provisos, including the label ceding greater creative control to the artist and a commitment to breaking Williams in the US market. In return, EMI affirmed they would benefit from a cut of Williams' non-recording activities, including touring, publishing, and merchandising, thus protecting the company from any commercial downturn in the singer's album sales. Williams claimed to be ecstatic and "richer beyond my wildest dreams", and his new album Escapology duly topped the UK charts the following month.
In August 2003, Robbie performed before 375,000 people during a three-day stint at Knebworth. The performance was the largest in British pop history. A live album of the event was soon released and promptly hit the Top Five in the UK, giving ample evidence to the popularity of the event. In December of that year, a DVD recording of one of the Knebworth shows was released, setting sales records throughout the UK and Australia.
Robbie's personal life has become the stuff of tabloid heaven as well, with his many romances frequently grabbing headlines -- Robbie has been romantically involved with a bevy of young beauties, including: former All Saints singer Nicole Appleton, model Rachel Hunter, and former Spice Girl Geri Halliwell.
In October 2004, Rob released a Greatest Hits album, with two new tracks on the CD. The first of these, "Radio", debuted at # 1 and the album itself hit # 1 several weeks later. In February 2005, Robbie won yet another Brit Award, as "Angels" was voted the Best British Song of the Past 25 Years. This gives him a record 15 Brit Awards.