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Having written and produced comedy rap songs in his early YouTube career, KSI has since recorded more serious releases, achieving four top 40 singles on the UK Singles Chart—two of which reached the top 10. His debut studio album Dissimulation was released on 22 May 2020. As an actor, KSI featured in the British comedy film Laid in America (2016), and was the subject of KSI: Can't Lose (2018), a documentary film following the build-up to his first amateur boxing fight.

On 3 September 2019, a rematch between the two was announced. The fight took place on 9 November 2019 at the Staples Center, Los Angeles, and was promoted by Eddie Hearn. Unlike the first fight, the rematch was a professional fight and the two fighters did not wear any headgear. The undercard featured professional boxers, including Devin Haney and Billy Joe Saunders. KSI trained under up-and-coming professional boxer, Viddal Riley, and Jeff Mayweather, uncle of Floyd Mayweather Jr.

Upon its announcement as a professional bout, the event drew criticism from a number of figures within boxing, as well as boxing journalists and fans, some of whom labelled the fight as an 'insult' to boxing. The headline accusation was that the pair were using the event as a 'cash grab' and questioned the 'legitimacy' of the match as a professional bout, and many questioned the choice of putting professional world-title bouts on the undercard beneath two YouTubers. Others within the sport, however, were more receptive to the fight and embraced the event. The executive director of the California State Athletic Commission (the fight's sanctioning body), Andy Foster, defended the accusation that the YouTubers weren't fit to fight professionally, saying in an interview that "If they weren’t YouTube stars, this fight is still approvable in every commission in this country as debut athletes". Kevin Draper of The New York Times noted KSI, Paul and the organisers' intention to bring a new audience to a 'stagnant' sport and highlights the fact both YouTubers sought coaching from world-champion boxers and trainers. Professional boxers Anthony Joshua, Deontay Wilder, Tyson Fury, Dillian Whyte and Andy Ruiz Jr. also expressed support for the event and the fact it was being held as a professional bout, highlighting the benefit it could bring to boxing in terms of expanding the sport's audience.

KSI announced on 28 February 2019 that he would be releasing a collaboration album with British YouTube rapper Randolph titled New Age, as well as going on a tour across the UK and some parts of Europe to promote the album. The album was proceeded by three singles: "Slow Motion", "Beerus" and "Red Alert". New Age was released independently on 12 April 2019 and features guest appearances from Jme, Talia Mar and Quadeca. The album debuted at number 17 on the UK Albums Chart and at number 1 on the UK R&B Albums Chart.

On 4 November 2019, it was announced that KSI had signed with RBC Records, under BMG Rights Management, in order to "take his music to the next level". On 7 November 2019, KSI released his first single under the new record label titled "Down Like That", featuring American rappers Rick Ross and Lil Baby and British singer and producer S-X. The track was performed live by the featured artists during KSI's ring walk for KSI vs. Logan Paul II on 9 November 2019. "Down Like That" peaked at number 10 on the UK Singles Chart, making it KSI's second highest-charting single in the UK to date, and it received a Silver certification from the BPI. Soon after, KSI confirmed that he had started working on his debut album and that "Down Like That" is the first single from the album. KSI released the album's second single, "Wake Up Call", featuring American rapper and singer Trippie Redd, on 31 January 2020. The song charted at number 11 on the UK Singles Chart, making it KSI's third highest-charting single in the UK to date. The album's third single, "Poppin", featuring American rappers Lil Pump and Smokepurpp, was released on 27 March 2020 and charted at number 43 on the UK Singles Chart. "Houdini", featuring British singer Swarmz and British rapper Tion Wayne, was released as the fourth single from the album on 24 April 2020. The song charted at number 6 on the UK Singles Chart, making it KSI's highest-charting single in the UK to date. KSI's debut studio album, titled Dissimulation, was released on 22 May 2020, followed by a deluxe edition three days later. The album's fifth single, "Cap", featuring American rapper Offset, was released on the same day as the album.

In 2019, KSI uploaded a video titled "Ending it all", from which all ad-revenue would be donated to various suicide-prevention charities.

British YouTuber, Joe Weller, criticised KSI and the Sidemen for artificially stirring friction between him and the Sidemen for views. Following resulting public disagreements on Twitter, the pair announced that they would be facing each other in a white-collar amateur boxing match on 3 February 2018 at Copper Box Arena in London. During the announcement, the two YouTubers verbally and physically confronted each other, with KSI appearing to mock Weller's struggles with depression; KSI later apologised for his comments. The fight, titled KSI vs. Joe Weller, was held on 3 February 2018 and was won by KSI 1 minute and 30 seconds into the third round by way of technical knockout; KSI was awarded the YouTube Boxing Championship Belt. On YouTube, the fight drew 1.6  million live viewers, 21  million views within a day, and over 25  million over the next several days, making it the biggest white-collar boxing fight in history. KSI expressed his respect for Weller after the fight for being "way harder, way tougher than I thought," and praised him for his commitment to raising awareness for mental health, before calling out American YouTuber Logan Paul, his brother Jake Paul, and retired footballer Rio Ferdinand.

On 24 February 2018, it was announced that KSI would be fighting Logan Paul in a white-collar amateur boxing match, with his brother, Deji, fighting Paul's younger brother Jake on the undercard. The fight ended as a majority draw, with two judges scoring the fight even at 57–57 and a third judge scoring 58–57 in favor of KSI. The fight, labelled "the largest event in YouTube history" and "the largest ever amateur boxing fight", sold-out 21,000 tickets for Manchester Arena, generating an estimated live gate revenue of over £2.7  million ($3.5 million ). It was watched by over 2.25  million viewers live, including over 1.05  million watching pay-per-view and 1.2 million watching illegal streams on Twitch. The event eventually received over 17  million online views on the official YouTube channel (pay-per-view and free-view) as of 18 September 2018, in addition to over 5  million viewers who watched illegal streams on Twitch as of 28 August 2018.

On 31 January 2018, KSI independently released a single titled "Uncontrollable", featuring British grime MC Big Zuu, alongside a music video, which has 29 million views. The song was used as KSI's ring walk entrance music for KSI vs. Joe Weller on 3 February 2018. The song charted at number 89 on the UK Singles Chart. KSI independently released his next single, "On Point", on 17 August 2018, alongside a music video, which has 38 million views. The song was used as KSI's ring walk entrance music for KSI vs. Logan Paul on 25 August 2018.

On 4 August 2017, KSI tweeted that he would be leaving the Sidemen, citing conflicts with fellow member, Ethan Payne. Shortly thereafter, he released a number of diss track videos criticising members of his then-former group, to which most of the members responded back with their own. Later that month, KSI released a video in which he claimed that he was being deported from the United States for receiving an incorrect visa. In November 2017, KSI released a video discussing whether his supposed falling out with the Sidemen was real or fake, saying, "[t]he drama wasn't entirely real but wasn't entirely fake either."

After taking a four-month hiatus from YouTube, on 25 June 2017, KSI independently released a single titled "Creature", alongside a music video, which has 25 million views. The song charted at number 100 on the UK Singles Chart. "Creature" was the first single from KSI's third EP, Space, which was released independently on 30 June 2017.

KSI released his fourth EP titled Disstracktions on 29 September 2017 through Island Records. The EP included the diss tracks "Earthquake", featuring American YouTuber and rapper Ricegum, "Little Boy", "Two Birds, One Stone" and "Adam's Apple". Disstracktions charted at number 31 on the UK Albums Chart and at number one on the UK R&B Albums Chart. KSI confirmed one week before the release of Disstracktions that it would be his final release with Island Records and that all future music would be released independently.

On 29 April 2016, KSI released a single titled "Goes Off", featuring British artist Mista Silva. The song is the first single from KSI's second EP titled Jump Around. KSI released the EP's second single, "Friends with Benefits", with Dutch EDM group MNDM, on 29 July 2016, alongside a music video which has 45 million views.The song charted at number 69 on the UK Singles Chart. The EP's title track, featuring American rapper Waka Flocka Flame, was released as the third single on 16 September 2016, alongside a music video which has 13 million views. The Jump Around EP was released on 28 October 2016 through Island Records. One of the EP's songs, "Touch Down", featuring rapper and singer Stefflon Don, was featured on the soundtrack of the 2017 film Baywatch.

KSI co-organised and participated in the three Sidemen charity football match events. The first match, played in 2016 at St Mary's Stadium, Southampton, raised £110,000 for the Saints Foundation. The second match, played in 2017 at The Valley Stadium, London, raised £210,000 for the NSPCC's Childline and Charlton Athletic Community Trust. The third and final match, played in 2018, again at The Valley Stadium, raised £65,747 through the JustGiving donation page alone (the total amount raised is unconfirmed) for Young Minds and Charlton Athletic Community Trust.

Having written and produced comedy–rap songs for his YouTube channel in 2011, KSI took his first major step into expanding his content beyond just YouTube videos in 2015 by starting his career as a serious musician and rapper. He releasing his debut song, "Lamborghini", written about his recently purchased Lamborghini Aventador, featuring P Money on 23 March 2015, reaching number 30 in the UK singles chart. Shortly after, KSI's debut EP, Keep Up, peaked at number 1 on the UK R&B Albums Chart and he has since released a number of songs and toured with his music. KSI further exapanded his content later that year, releasing a biography titled KSI: I Am a Bellend. The book was released on 24 September 2015 in the UK and five days later in the United States, and KSI toured to support the book from its release until 4 October 2015. In 2016, KSI and the Sidemen published Sidemen: The Book, which sold 26,436 copies within three days and topped the hardback nonfiction charts.

KSI released his debut single titled "Lamborghini", which features British grime MC P Money, on 23 March 2015 through British musician Sway's record label Dcypha Productions, alongside a music video, which has 110 million views. The song charted at number 30 on the UK Singles Chart. On 29 October 2015, KSI announced his debut extended play (EP) titled Keep Up. The EP's title track, which features British grime MC Jme, was released on 13 November 2015, alongside a music video which has 40 million views, and reached number 45 on the UK Singles Chart. The EP was released on 8 January 2016 through Island Records and debuted at number 13 on the UK Albums Chart and at number one on the UK R&B Albums Chart.

KSI has utilised his wealth and influence to support a number of charitable causes in his career. In 2015, KSI donated $10,000 to an online charity stream done by YouTuber Castro1021, and participated in the Race Against Slime event, raising money for SpecialEffect, a foundation developing technology to aid people with physical disabilities to play video games.

His younger brother, Deji Olatunji, is also a YouTuber. The brothers ranked first and second respectively as the "UK's Most Influential YouTube Creators" by Tubular Labs in 2015. In late November 2018, Deji revealed KSI's personal bank records in a video; KSI later condemned Deji's actions and expressed his disappointment towards his parents for allowing the publication of his financial records. In January 2019, Deji apologised to his brother for his "impulsive" and "rash" behaviour and made the video private. In May 2019, Deji made the video public again, prompting KSI to state on Twitter that he is "done" with his brother. In November 2019, KSI revealed that their feud was settled, stating that "brothers fight and there's always gonna be a situation where, because we're in the public eye, everything gets blown out of proportion".

KSI's income for 2014 was reported to be $1.12 million. In 2015, KSI's earnings were estimated by Forbes as over $4.5 million, ranking him as the fifth-highest paid YouTuber in the world. Within two years, his wealth had more than doubled as his net worth reached $11 Million by 2017. In 2018, Esquire magazine reported that, according to Social Blade, KSI can make up to £250,000 in advertising revenue from one video and that product endorsements on his social media cost around £75,000. Heavy reported in the same year that KSI was the director of three UK companies with equity totalling $2.2 million (£1.7 million). In an interview with Men's Health, KSI confirmed that he also owns over ten properties "all around England" with a combined worth of over $10 million. In late 2019, the Daily Mirror estimated KSI's net worth to be around $20 million. In 2020, The Times estimated KSI's earnings to be £12 million a year.

In 2014, KSI and three other members of the Sidemen – Simon Minter, Josh Bradley and Vik Barn, respectively known on YouTube as Miniminter, Zerkaa and VikkStar123 – moved into a house in London, before moving into a new house in London in 2016. In 2019, they moved out of the house, with KSI and Minter moving into an apartment in central London.

In October 2013, KSI signed with Maker Studios' sub-network, Polaris. Later that month, on 19 October 2013, KSI and four other British YouTubers formed the entertainment collective Ultimate Sidemen, later shortened to just Sidemen. Since 2014, the group has consisted of seven British YouTubers: Vikram Barn (Vikkstar123), Josh Bradley (ZerkaaHD), Tobi Brown (TBJZL), Harry Lewis (W2S), Simon Minter (Miniminter), Ethan Payne (Behzinga), and KSI. The group produces online videos, most often consisting of challenges, sketches and video-game commentary, as well as selling exclusive Sidemen merchandise.

After six three minute rounds, KSI was the winner via split decision, with two judges scoring the fight 57–54 and 56–55 for KSI, while the third judge scored it 56–55 in favour of Paul. Paul and KSI shook hands and shared an embrace after the fight, with both paying respect to one another, though Paul stated his intention to contest the commission for his point deduction for his illegal punches, stating that he does not dispute what happened but thought he deserved only a warning. When asked about a possible rematch, Paul expressed his support for the idea, but KSI rejected any prospect of a third fight against Paul, saying "It's done ... I'm on to the next thing".

KSI's initial rise to fame was not without controversy. He was widely criticised for his so-called 'rape-face', a recurring joke on his channel during 2012 and 2013, and was the centre of a controversy following his actions at a Eurogamer event in 2012. Accused of verbally and sexually harassing staff and attendees at the event, Microsoft cut ties with KSI and he was banned from all future Eurogamer events. KSI subsequently apologised "for any offence the video of 15 months ago may have caused in the short time it was on his YouTube channel, references to it since and subsequently used by other people" and stated his desire to move on from the incident and be "be judged on the great content and value he gives to brands and partners, without controversy."

In 2009, KSI registered his YouTube account under the name KSIOlajideBT. KSI built his following from posting gaming-commentary videos of the FIFA video game series, although as his following has grown, his YouTube content has diversified to include more vlog and comedy style videos. As of May 2020, the channel has received over 21 million subscribers and over 5 billion video views. In 2019, he was ranked as the second most influential online creator in the United Kingdom by The Times.

Olatunji registered his current YouTube account on 24 July 2009 under the name KSIOlajideBT (which would later be shortened to simply "KSI"), where, inspired by other YouTubers, he uploaded gaming–commentary videos of the FIFA video game series from his bedroom at his parents' house in Watford. After sharing his videos with friends and on online forums, KSI grew a small following of around 20,000 after two years. Introducing more vlog-style content and playing a variety of games over the next year saw his following grow more rapidly as he reached 1 million subscribers just three years after founding his channel. By the end of 2013, KSI's subscriber count surpassed 3 million, making him the then twenty-fifth-most subscribed user on YouTube. The same year, KSI visited Las Vegas, where he discussed YouTube's launching of a paid-channel subscription project.

Olajide Olayinka Williams "JJ" Olatunji (/ɒ l ə ˈ dʒ iː d eɪ ɒ l ə ˈ t u n dʒ iː / , oh-lah-JEE -day oh-lah-TUHN -jee; born 19 June 1993), better known as KSI, is an English YouTuber, internet personality, rapper, actor, and boxer. He is also a member and co-founder of the British YouTube group known as the Sidemen.

Olajide Olayinka Williams Olatunji was born on 19 June 1993 to Nigerian parents Jide Olatunji and Yinka Olatunji. He was born and raised in Watford, Hertfordshire. He was educated at Berkhamsted School in Berkhamsted, Hertfordshire, where he met future Sidemen member Simon Minter. Olatunji registered his first account on YouTube under the name "JideJunior" in 2008 while in his early teens, before opening his current channel in 2009. Olatunji dropped out of sixth form college to pursue his YouTube career once he was earning steady monthly revenue from his uploads. In an interview in 2014, he recounted, "I asked the teacher, 'Should I leave?' He asked, 'How much are you making from YouTube?' and I said, 'Around £1,500 a month.' He told me he was getting less than that." His parents disapproved, but have since become supportive and have featured in a number of his videos.