Rise to Success: Career Highlights of Olivia Dean

How Olivia Dean built a successful career. Explore key moments that defined the journey.

Olivia Dean is a rising British singer-songwriter known for her soulful blend of neo-soul, jazz, and pop. Emerging from London and a graduate of the BRIT School, she gained significant recognition for her conversational, emotive songwriting and authentic performance style. Her breakthrough came with EP releases like 'Ok Love You Bye' and 'What Am I Gonna Do on Sundays?', which showcased her ability to blend intimate storytelling with warm, melodic arrangements. In 2023, she released her highly anticipated debut studio album, 'Messy,' which earned critical acclaim and a nomination for the Mercury Prize. Dean is celebrated for her charismatic stage presence and her ability to articulate the nuances of modern relationships and personal growth. As a prominent figure in the UK music scene, she is frequently lauded for her artistic integrity and her unique, genre-bending vocal delivery, solidifying her status as one of Britain's most compelling new voices.

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Full Timeline Career & Achievements

2017: Sziget Festival Debut Performance

In 2017, Olivia Dean reached a career milestone by performing her first show at the Sziget Festival in Hungary, playing for an audience of 16,000 people.

October 2018: Self-release of debut single

In October 2018, Olivia Dean officially launched her music career by self-releasing her debut single titled "Reason to Stay."

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January 2019: Feature on Rudimental single

In January 2019, Olivia Dean appeared as a featured artist on the song "Adrenaline," which was included on the Rudimental album "Toast to Our Differences."

November 2019: Release of OK Love You Bye EP

In November 2019, Olivia Dean released the single "OK Love You Bye" followed by her debut EP of the same name, which was recorded in a converted East London pub.

2019: Signing with AMF and Virgin EMI

In 2019, following the viral success of her self-released song "Reason to Stay," Olivia Dean officially signed recording contracts with AMF Records and Virgin EMI Records.

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August 2020: From Me to You tour

In August 2020, amidst the COVID-19 pandemic, Olivia Dean embarked on a DIY-style concert series titled the "From Me to You" tour. Traveling across the UK in a branded yellow truck, she provided intimate, open-air performances for small groups of fans and local residents.

December 2020: Release of What Am I Gonna Do On Sundays?

In December 2020, Olivia Dean released her second extended play (EP) titled "What Am I Gonna Do On Sundays?", marking a significant milestone in her musical career during the pandemic.

2020: Mother's appointment as Deputy Leader of the Women's Equality Party

In 2020, Olivia Dean's mother made history by becoming the deputy leader of the Women's Equality Party, marking the first time a Black woman held the position of deputy leader for a political party in Europe.

April 2021: Breakthrough Artist Recognition and Viral Performance

In April 2021, Olivia Dean was honored as the breakthrough artist of the year by Amazon Music and returned to live performances at The Jazz Cafe, with a recording of the show gaining viral status on TikTok.

August 2021: Revive Live Tour Participation

During August 2021, Olivia Dean performed six concerts across southern England as part of the Revive Live Tour, an initiative supported by the Music Venue Trust and The National Lottery to assist live music venues.

November 2021: Release of The Christmas Song

In November 2021, Olivia Dean recorded a rendition of The Christmas Song for Amazon's Christmas Originals, which successfully charted at number 19 on the UK singles chart.

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May 2023: BBC Big Weekend and TV Debut

In May 2023, Olivia Dean performed at BBC Radio 1's Big Weekend and made her television debut on Later... with Jools Holland, where she performed her single Dive.

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November 2023: BBC Music Introducing Artist of the Year

In November 2023, Olivia Dean achieved a significant career milestone by being selected as the BBC Music Introducing Artist of the Year.

2023: Shift in Music Video Production Strategy

In 2023, Olivia Dean ended her practice of exclusively working with female directors for her music video productions, a tradition she had upheld to reflect her strong feminist values.

2023: Release of debut album Messy

In 2023, Olivia Dean released her critically acclaimed debut studio album, Messy, which garnered a nomination for the prestigious Mercury Prize.

June 2024: Release of single Time

In June 2024, Olivia Dean expanded her discography with the official release of her single titled Time.

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February 2025: Release of It Isn't Perfect But It Might Be and Laneway Festival tour

In February 2025, Olivia Dean released the single "It Isn't Perfect But It Might Be" for the soundtrack of the film Bridget Jones: Mad About the Boy. Additionally, during February 2025, Dean made her debut in Australia and New Zealand by performing at all six dates of the Laneway Festival, with stops in Auckland, Brisbane, Sydney, Melbourne, and Perth.

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August 2025: Support performance on Sam Fender's People Watching Tour

During August 2025, Olivia Dean continued her support role for Sam Fender's People Watching Tour, which included high-profile performances at venues such as London Stadium and St James' Park.

September 2025: Release of The Art of Loving

In September 2025, Olivia Dean released her second studio album, The Art of Loving, which featured several successful singles including "Man I Need." This release led to a significant career achievement, as she became the first female solo artist to hold four singles in the UK Top 10 chart simultaneously.

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November 2025: Announcement and Ticketing Controversy for The Art of Loving Live Tour

In November 2025, Olivia Dean announced 'The Art of Loving Live' tour spanning 29 cities across the U.S. and Europe. The tour launch faced significant backlash due to Ticketmaster queues and predatory resale pricing. Dean publicly denounced Ticketmaster, Live Nation, AXS, and the Anschutz Entertainment Group for these exploitative practices. Following her criticism, Ticketmaster and AXS implemented resale price caps and issued refunds to affected fans in November 2025.

2025: Success of The Art of Loving

In 2025, Olivia Dean achieved significant commercial success with her second album, The Art of Loving, which topped the UK Albums Chart. The era included the chart-topping single "Man I Need" and saw her become the first female solo artist to hold four singles in the UK top ten simultaneously, including "Nice to Each Other," "So Easy (To Fall in Love)," and "Rein Me In."

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January 2026: Billboard Rookie of the Year and Graham Norton Show Performance

In January 2026, Olivia Dean was honored as the Rookie of the Year by Billboard and showcased her talent with a performance of "So Easy (To Fall in Love)" on The Graham Norton Show.

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February 2026: Brit Awards Success and Grammy Win

In February 2026, Olivia Dean achieved significant recognition by winning four awards at the 46th Brit Awards and securing the Grammy Award for Best New Artist.

February 2026: Grammy Award for Best New Artist Win

In February 2026, Olivia Dean won the Grammy Award for Best New Artist and utilized her acceptance speech to honor her grandmother, Carmen, a member of the Windrush generation, while advocating for the positive contributions of immigrants.

March 2026: Hourglass Global Brand Partnership Announcement

In March 2026, it was officially announced that Olivia Dean had been appointed as the Global Brand Partner for the cosmetics company Hourglass.

July 2026: Record-Breaking Success of Rein Me In

By July 2026, the song "Rein Me In" by Dean and Sam Fender reached 16 weeks at number one on the UK charts, becoming the longest-running number one by a British act and tying for the second-longest-running number-one single of all time.