2005–2009: Lessons to Be Learned The tracks "Don't Tell Me" and "Sorry", co-written with Barbara and Adrian Hannan, appeared on the soundtrack of 2005 Australian film
Hating Alison Ashley. The first single, "Sweet About Me", debuted on the
UK Singles Chart that month and climbed to number six three months later, in June. It reached number seventeen on the
Irish Singles Chart, and peaked at number one on the Australian ARIA Singles Chart. The song was used in a worldwide advertising campaign for the deodorant Sure/Rexona. Cilmi's second UK single, "Save the Lies", was not as successful as "Sweet About Me", peaking at number thirty-three in the UK. In Australia, the second single from the album was "
Don't Wanna Go to Bed Now", which reached number twenty-eight. The subsequent single, "Sanctuary", was issued in November 2008 and failed to chart. From March to May 2008, Cilmi supported the Sugababes on their UK
Change Tour. She opened for
James Blunt on his June 2008 Australian tour, and participated in the October 2008
MTV Greece concert alongside
R.E.M. and
Kaiser Chiefs. Also in 2008, Cilmi won six
ARIA Music Awards in Australia, taking Best Female Artist, Breakthrough Artist – Single ("Sweet About Me"), Breakthrough Artist – Album (
Lessons to Be Learned), Best Pop Release (
Lessons to Be Learned), Highest Selling Single ("Sweet About Me"), and Single of the Year ("Sweet About Me"). Cilmi covered the
Connie Francis song "Warm This Winter", originally a minor hit for Francis in 1962 as "
I'm Gonna Be Warm This Winter", for
Co-operative's Christmas 2008 advertising campaign; released as a single, it reached number twenty-two on the UK Singles Chart. In January 2009, Cilmi was nominated in the International Female category at the
BRIT Awards and sang in the
Rod Laver Arena before the
2009 Australian Open men's final. Cilmi performed at the
Melbourne Cricket Ground in March 2009 for
Sound Relief, a multi-venue rock music concert in support of relief for the
Victorian bushfire crisis. The event was held simultaneously with a concert at the
Sydney Cricket Ground. The song "Let Me Know" was described as the "Lessons to Be Learned-ish" song of the album. It also featured a new version of "Sweet About Me", with some disco/electronic style to show the change in her music. While producing the album, Cilmi worked with
Greg Kurstin, The Invisible Men and
Dallas Austin, as well as
Xenomania. She made her debut in producing with the track "Love Me Coz", saying that it was the song she was most proud of due to the fact it was produced with her band. The third single, "
Defender", was released in August 2010 accompanied by a B-side track, "
Magic Carpet Ride", but both singles failed to make impact on the charts. Cilmi's version of "Magic Carpet Ride" was featured over the closing credits of British film
Soulboy. Cilmi supported English singer
Leona Lewis on the UK leg of her 2010
The Labyrinth Tour.
Popjustice named
Ten as their fourth-best album of 2010.
2010–2025: The Sting, All Kings and Queens and The Water EP By October 2010, Cilmi had already begun work on her third studio album. She has been quoted as saying: "It's totally exciting because I am spending a bit more time with this record. I want to see what works. I really love
Dolly Parton,
roots music,
Tricky and
Enya, so anything could happen." On 20 January 2012, Cilmi released an acoustic version of a song from her album, "Vicious Love". It is played in a clip video where she sings with her band and walks around an Italian restaurant with sunglasses. Two days after the broadcast, she says: "This is an 'Acoustic-ish' version of a tune that will be on the new record, one that I love very much". The song has blues influences, contrasting the disco-inspired pop sound of
Ten. Cilmi claims she felt pressured into adopting a more sexual image, which prompted her to part ways with Island Records and her management team. She also told the
Herald Sun that the lacklustre commercial reception of her second album,
Ten, taught her not to compromise herself or her music: "It was an awakening for me to realise the position I am in to make the record that I want to make and just stand up for myself." On 22 January 2012, Cilmi explained how the song "Vicious Love" was inspired. She states: "If you've ever experienced any type of 'Vicious Love' you will know that sometimes despite all the arrows pointing to a dead end there is just no way out, there is no way back. But then again don't all roads lead to dead ends? Guess we should just enjoy the ride..." In March 2013, Cilmi first performed "Sweet About Me", as well as two new songs "Come Wander With Me" and "Sweeter in History", at the Moxafrica Festival. On 15 March, the video from her new single "Sweeter in History", premiered on her YouTube page. The video was shot in Italy, precisely in
Cassino and Valvori,
Lazio. In July 2013, Cilmi announced a new track called "The Sting", released on 2 September as the album's lead single. "
Symmetry" was released on 11 November as the album's second single. In April 2015, Cilmi announced that she would be performing with her brother Joseph under the name All Kings and Queens, and released the single "Voodoo" in September 2015. In 2018, single "Push" was released. In June 2019, Cilmi posted a series of Instagram posts, explaining her desire to return to music and that she was in the process of completing new songs. On 1 July, Cilmi shared the first teaser for her new single titled "Ruins", which was released on 5 July 2019 with a music video released on 16 July 2019. Cilmi announced she would be playing her first solo gig since 2014 at
St Pancras New Church in London. Cilmi kicked off the promotion of her first new single in six years by appearing on ITV News, London Live and BBC Radio London. The track made its debut on
BBC Radio 2. Cilmi took part in live sessions on BBC Radio 2 and BBC Radio 5 Live. She appeared on the
James Whale show on
Talkradio on 12 August 2019. Cilmi released her EP,
The Water on 1 November 2019. In an interview for the EP, Cilmi stated, "For this EP, I wanted to take things back to basics....When I went back and listened to my favourite records I realised there's no fancy production and the songs weren't written sitting in front of a computer playing a loop back and forward....these were songs that were written prior to being recorded in the studio....We recorded the songs onto my mobile phone into a folder called 'Skeletons' until it was time to go into the studio." In 2020 she started ''Chillin' With Cilmi'' during the pandemic and she has plans to tour again and celebrated her streaming numbers at the end of 2022, in Europe, UK and Australia. In February 2025, Cilmi toured alongside
Delta Goodrem and
The Corrs on the Australian leg of their tour.
2026-Present: Pure Love and forthcoming studio album In February 2026, Cilmi performed as the opening act for
Jack Savoretti and
Katherine Jenkins, in honor of the
War Child charity benefit concert. On 24 April 2026, Cilmi released her first music in almost 7 years - "Pure Love" - which will be the lead single for her forthcoming new studio album, which will be released on
V2 Records. Cilmi described the song as "coming home to yourself". ==Artistry==