Inspired by the US and UK hip-hop music, Skepta started his music career by emceeing at rap performances, and appearing on pirate radios. He worked as a DJ in Meridian Crew, a Tottenham-based grime crew. During that time, he released a number of instrumentals including the ‘DTI (Pirate Station Anthem)’ and ‘Private Caller’.
After Meridian Crew was disbanded in 2005, Skepta, his brother Jme and fellow rapper Joseph Bamber joined Roll Deep, a grime crew.
In 2006, Skepta, along with Jme, started ‘Boy Better Know’, an English grime collective and record label. It was founded in North London as an independent record label. The members of the collective also published their music through this record label.
After the formation of ‘Boy Better Know’, Skepta did a competition with fellow MC Devilman for the DVD ‘Lord of the Mics 2.’ The clash is still remembered as one of the biggest clashes in grime history. After the successful clash, he released a mixtape titled ‘Joseph Junior Adenuga.’
He released his debut album ‘Greatest Hits’ on September 17, 2007, through ‘Boy Better Know’. On September 15, 2008, he independently released ‘Rolex Sweep’ as a digital download. It became the lead single from his second studio album ‘Microphone Champion’. ‘Rolex Sweep’ peaked at No. 86 on the UK Singles Chart.
He released his second studio album ‘Microphone Champion’ on June 1, 2009. The album included ‘Rolex Sweep’, which was the first single of the album to be released on September 15, 2008. It peaked at No. 86 on the UK Singles Chart.
‘Too Many Man’, the second single from the album, was released on May 18, 2009, which reached No. 79 on the UK Singles Chart. The third single from the album, ‘Lush’, was released on October 12, 2009.
His third studio album ‘Doin' It Again’, was released on January 31, 2011, on Boy Better Know. Prior to the album’s release, five singles were released, four of which appeared on the UK Top 40 Singles chart.
'Bad Boy’ was the lead song, which was released as a digital download on March 15, 2010. ‘Rescue Me’, the second single, was released as a digital download on June 27, 2010. The third single, ‘Cross My Heart’, which featured vocals by singer Preeya Kalidas, was also released as a digital download on October 17, 2010.
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The fourth song ‘So Alive’ was released as a single on February 6, 2011. ‘Amnesia’, the fifth single, was released on February 27, 2011. It reached No.164 on the UK Singles Chart. ‘Rescue Me’ was the most successful, and peaked at No.14.
In 2012, he released two singles from his upcoming fourth album—‘Hold On’ and ‘Make Peace Not War’. The singles found placed in the Top 40 charting singles in the UK. After a lukewarm response from the first two singles, he released a mixtape ‘Blacklisted’ on December 2, 2012.
On June 8, 2014, he released a single, ‘That's Not Me’, which featured his brother Jme. The single peaked at No. 21 on the UK charts. It later became the lead single from his fourth album ‘Konnichiwa’. That same month, he did a verse for the remix of ‘German Whip’ by Meridian Dan.
In 2014, he released another single ‘It Ain't Safe’, followed by ‘Shutdown’ in 2015. On February 14, 2016 he released the single ‘Ladies Hit Squad’, which featured American rapper A$AP Nast and grime artist D Double E.
On May 6, 2016, ‘Boy Better Know’ released Skepta’s fourth studio album ‘Konnichiwa’. The album was launched at a party in Tokyo, and Skepta performed the complete album live. The album had four major singles, out of which ‘That's Not Me’, ‘Shutdown’ and ‘Man’ reached the Top 40 charts.
The album received widespread acclaim from critics. It was also included in a number of top albums lists of 2016 on the international level. ‘The Guardian’ and ‘Apple Music’ named it as the best album of 2016.
In April 2017, he began his ‘Banned From America’ tour. It included 14 shows in the US and Europe. The tour had been named as such because his earlier US tour was canceled as his visa to enter the US was denied.