Confessions of a Pop Group is the fourth full-length studio album by the English sophisti-pop band the Style Council, released 20 June 1988 by Polydor. After the critical failure of The Cost of Loving (1987), tensions between Polydor and lead singer Paul Weller intensified, but Polydor paid Weller a hefty advance for the recording of Confessions. Backing vocalist Dee C. Lee became an official member during the sessions, while drummer Steve White left the group. The sessions were engineered by "Jezar" using two 24-track digital recorders, which allowed the group to experiment in ways they had not previously engaged before.

Confessions is split into two sides, the first side (The Piano Paintings) featuring pieces inspired by jazz and classical music, and the second side (also titled Confessions of a Pop Group) featuring a more familiar, upbeat funk sound. The stylistic differences between the two sides is an idea not unlike that employed on the first record Café Bleu. Its usage of suites has led some to consider it similar to a concept album. Weller was inspired by numerous artists on the album, including composer Erik Satie and the Beach Boys, and his socially conscious lyrics on the album are unusually vitriolic and bitter. Each song on the album is accompanied in the liner notes by a painting by Dan Davies.

With no hit singles and an unusual promotional strategy, Confessions was a relative commercial failure for the band, reaching only number 15 on the UK Albums Chart. The album received mixed reviews, with some citing its ambitions as successful and others feeling they were self-indulgent. In the years since its release, the album has seen numerous reappraisals, with some critics posing it as the band's best album and as one which captured the mood of late 1980s Great Britain. Weller continues to think highly of the album. It has been re-released several times. "How She Threw It All Away" and "Why I Went Missing" are often cited as lost Weller classics, having not been played live since the early 'rebirth' of Weller's solo career (around 1990/91). A key track from the album, "It's A Very Deep Sea," was featured when a reunited Style Council played the song at the end of a 2019 documentary about their work.

After achieving critical and commercial success in 1985 and 1986, the Style Council's third full-length album, The Cost of Loving, was released in February 1987 to commercial success, reaching number 2 in the UK Albums Chart, but to hostile reviews from music critics. The album, which featured soul music and American-style R&B inspired by Jimmy Jam and Terry Lewis, was dismissed by one later critic as "bland," and several years later, the NME included the album in a list of fourteen albums that "should've been an EP". Later on in 1987, Red Wedge, a collective of musicians, including Style Council lead singer and writer Paul Weller, who had gathered to help spread support for the Labour Party among young voters, failed to displace the Conservative Party in the 1987 general election, and the collective soon disbanded.

The band's popularity was fading and the group were regularly being ridiculed in the music press, with criticism being aimed at Weller in particular. Tension between Weller and the band's record label Polydor was also prevalent, with the label becoming impatient with Weller's esoteric choices regarding musical direction and artwork. Weller was becoming more musically ambitious, and in early 1988 he and fellow band member Mick Talbot composed the songs for the band's fourth album, Confessions of a Pop Group, their most musically challenging project to date. The band set for recording the album with Polydor paying Weller a reluctant advance of £500,000. Tension between Weller and Polydor was especially prominent during the album's recording sessions.

Long time guest vocalist Dee C. Lee, who was pregnant with Weller's child and would soon become his wife, became an official member prior to the recording of the album, whereas drummer Steve White left the band to pursue a career with saxophonist Alan Barnes as the Jazz Renegades, who performed hard bop and Afro-Latin music. This left the Style Council to become a trio of Weller, Talbot and Lee. However, White still plays the drums on four songs on the album.

Weller and Talbot chose to produce Confessions of a Pop Group alone so they could avoid arguments with outside producers, which had been an occurrence in previous recording sessions for the group. Weller elaborated, saying that self-producing Confessions was always their intention: "We don't like to repeat ourselves, we believe that progression is the most important thing." Jezar engineered the album and later described the sessions as "deeply satisfying on an emotional level." After his experiences working on The Cost of Loving, Weller was more confident with Confessions and told Jezar about things he wanted to try out for the first time, including classical concert harp on the song "The Gardener of Eden" and a capella vocals reminiscent of a barber shop quartet on "The Story of Someone's Shoe". Jezar later cited Confessions as raising the bar "of what we tried to achieve."

Jezar created a digital multitrack recorder setup using 48 tracks set across two separate 24-track Sony 3324 machines, giving him and the band the technical capability to try several things in the sessions they had not before. Using two 24-track machines rather than one 48-track machine allowed the band to use more production techniques on the album, including, in Jezar's recollection, "making perfect backup copies of projects, no cross-talk limitations (no need to plan what was recorded adjacent to a timecode track), being able to copy tracks further forward or further backwards in time (to change the musical 'feel'), back-up of multiple tracks (i.e. vocals) after you'd bounced or composited them down to free-up space, spinning-in (copy and paste) of one-off riffs and musical sections into other parts of a song, non destructive editing of multitracks [and] immensely complex, overlapping multitrack edits." He later said: