Heavy Soul, the follow-up to the million-selling Stanley Road, saw Weller twist his sound again. The album was more raw than its predecessor; Weller was now frequently playing live in the studio in as few takes as possible.[citation needed] The first single "Peacock Suit" reached No. 5 in the UK Singles Chart, and the album reached No. 2. Success in the charts also came from compilations: "Best Of" albums by the Jam and the Style Council charted, and in 1998 his own solo collection Modern Classics was a substantial success.

In 2000, while living in Send, Surrey, he released his fifth solo studio album, Heliocentric. Once again finding himself without a record contract, Weller's Days of Speed worldwide tour provided him with the opportunity to view his works as one back catalogue, giving rise to a second successful live album in 2001. Days of Speed contained live acoustic versions from the world tour of the same name, including some of his best-known songs from his solo career and the back catalogues of his Jam and Style Council days.

There were rumours at the time that Heliocentric would be Weller's final studio effort, but these proved unfounded when he released the No. 1 hit album Illumination in September 2002. Co-produced by Noonday Underground's Simon Dine, it was preceded by yet another top 10 hit single "It's Written in the Stars". Weller also appears on the 2002 Noonday Underground album called Surface Noise, singing on the track "I'll Walk Right On".

In 2002, Weller collaborated with Terry Callier on the single "Brother to Brother", which featured on Callier's album Speak Your Peace. In 2003, Weller teamed up with electronic rock duo Death in Vegas on a cover of Gene Clark's "So You Say You Lost Your Baby", which featured on their Scorpio Rising album.