She recorded several pop hits in the 1980s and 1990s, including "There's a Guy Works Down the Chip Shop Swears He's Elvis" and cover versions of Billy Bragg's "A New England" and the Kinks' "Days".

She had a number 14 UK hit with "There's a Guy Works Down the Chip Shop Swears He's Elvis",[6] from her critically acclaimed debut album Desperate Character.

She returned to Stiff, where pop singles such as "Terry" and "He's on the Beach" were unsuccessful, but a cover of Billy Bragg's "A New England" in 1985 reached number 7 on the UK charts.

Also around this time, MacColl wrote and performed the theme song "London Girls" for Channel 4's short-lived sitcom Dream Stuffing (1984).

Ullman also recorded three more of MacColl's songs, "You Broke My Heart In 17 Places" and "You Caught Me Out", as the title tracks of her first and second albums respectively, and "Terry" which was released as a single in 1985.

However, she had regular session work as a backing vocalist, and she frequently sang on records produced or engineered by her husband, Steve Lillywhite, including tracks for The Rolling Stones on the Dirty Work album, Robert Plant, the Smiths, Alison Moyet, Shriekback, Simple Minds, Talking Heads, Big Country, Anni-Frid Lyngstad (of ABBA) and the Wonder Stuff, among others.

[13] MacColl re-emerged in the British charts in December 1987, reaching number 2 with the Pogues on "Fairytale of New York", singing a duet with Shane MacGowan.

After the contract issue was resolved, MacColl returned to recording as a solo artist and received critical acclaim upon the release of Kite (LP) in 1989.

Although Kite contained many original compositions, MacColl's biggest chart success from the album was the cover of the Kinks' song "Days", which gave her a UK top 20 hit in July 1989.

During this time, MacColl featured on the British TV sketch comedy French and Saunders, appearing as herself, singing songs including "15 Minutes" and "Don't Come the Cowboy with Me Sonny Jim!"

After MacColl’s death a memorial bench was placed in Soho Square inscribed with a lyric from the song where fans could pay their respects.

[16] In 1995, she released two new singles on Virgin, "Caroline" and a cover of Lou Reed's "Perfect Day" (a duet with Evan Dando), together with the "best of" compilation Galore.

After several trips to Cuba and Brazil, MacColl recorded the world music-inspired (particularly Cuban and other Latin American forms) Tropical Brainstorm, which was released in 2000 to critical acclaim.

She also made regular appearances on Jools Holland's TV shows, also on the BBC, singing during the 1995 Hootenanny a rendition of "Miss Otis Regrets" with the Pipes and Drums of the Irish Guards.

Her last television concert was recorded in Glasgow on 14 March 2000 and was broadcast by BBC, in December 2001, as Kirsty MacColl: The Boxed Set.

[17][18] In 2000, after she participated in the presentation of a radio programme for the BBC in Cuba,[19] MacColl took a holiday in Cozumel, Mexico, with her sons and her boyfriend, musician James Knight.

The powerboat involved in the collision was controlled by Guillermo González Nova, multimillionaire president of the Comercial Mexicana supermarket chain, who was on board with members of his family.

The campaign's remaining funds were to be divided between two charities, Casa Alianza México and Cuba Music Solidarity, a gesture of which, the statement read, "Kirsty would have approved".

Every year on the Sunday nearest to MacColl's birthday, 10 October, fans from all over the world hold a gathering at the bench to pay tribute to her and sing her songs.

[29] MacColl was honoured in 2002 with a memorial concert in London at the Royal Festival Hall, featuring a number of musicians who had worked with her or been influenced by her.

A similar memorial concert took place on her birthday (10 October 2010) at the O2 Shepherd's Bush Empire, to support her favourite charity, The Music Fund for Cuba.

On 7 August 2005, The Best of Kirsty MacColl, a single-disc compilation that included a "new" single, "Sun on the Water", made its debut on the UK album charts at number 17, climbing to No.

[33] On 13 December 2023, The Pogues reissued the song as a charity 7-inch single in tribute to MacGowan and to benefit the Dublin Simon Community, an organisation fighting homelessness.