In February 2014, PUREBOY was introduced by IT Entertainment as an 11-member boy group, previously having a total of 15 members the agency intended to debut. PUREBOY was initially intended as a rebrand or reformation of their first boy group PURE but they practically became an entirely new group as only Giho joined the group. On April 29, they had their first release as an eleven-member group with the special single "All Together", collaborating with IT Entertainment artists The Soul and The Peace, to commemorate the tragedy of the .
All of the proceeds from the song were donated to Sewol Ferry Victims. On May 7, the group was embroiled in controversy as a member was seen laughing and wearing flashy outfit during their visit to Paengmok Port. The agency later had to apologize and promised to be more careful.
On November 19, PUREBOY made their official debut in South Korea with their first digital single "Yellow Shirt". The lineup consisted of Sangyun, Hayoung, Sangmin, Nankang, Jiho, Youngbin, Jinseong, Hyobin and Jaewon. Later that year, they released their sole mini album White Snow on December 23, 2014, which became a sensation on Japan's Tower Records, peaking at No.
3 on their Tower Records K-Pop Chart for two consecutive weeks. In January 2015, it was reported that a significant number of important documents were stolen from IT Entertainment's office, including the members’ contracts, documents for entering Japan, IDs, and copies of passports. In February, new member Seokyu joined the group, making them a ten-member boy group.
On July 1, they released their Japanese debut single "LOVE x EVOL". In July, the agency made a surprise announcement that PUREBOY’s sub-unit PURE-L, then known as PUREBOY-L, would make their debut that fall. The lineup consisted of Jinwoo (later known as Jinu), Seokyu, Daewoong, Geumyong (later known as KI-O), Hojong, Yongjin (later known as Haru), Juyoung and Minho (later known as EnL).
Subsequently, all of their upcoming activities had to be cancelled. On October 25, it was revealed that the members who previously left PUREBOY had formed a new group named NAUGHTY BOYS. On December 10, PURE-L made their debut as six with the digital single "Balloons".
The lineup consisted of Seokyu, Jinu, Haru, Ki-O, Hojong and EnL. On January 28, 2016, IT Entertainment filed a lawsuit for damages and an injunction to ban activities against NAUGHTY BOYS. With this, PUREBOY became a nine-member group and the agency announced that PURE-L would merge back into PUREBOY and would maybe promote as a sub-unit again in the future if the time was right.
In the same announcement, they also revealed plans for a new sub-unit called Pure Boy O, centered around Sangyun and Hayoung. Furthermore, IT Entertainment announced that PUREBOY would be re-organized into a rotational group with no set limits on the number of total members, in addition to a planned sub-unit once the group added more members. Sometime later, Kunhee was recruited as a new member.
At the time, IT Entertainment had hoped that since they had nine members once again and an official second generation lineup, the group would be able to make a recovery, dubbed PUREBOY 2 and PUREBOY REBORN. On September 3, it was reported in the news that three members of NAUGHTY BOYS (the former PUREBOY members), only reported as Hwang, Jeon and Yang, were sent to the prosecution with a recommendation for indictment on charges of assaulting fellow PUREBOY member Seokyu on several occasions. Additionally, their manager K was under investigation for obstruction of business, and manager Y was under investigation for threats and extortion against members Hayoung and Sangyun.
On September 20, it was announced that Hwang, Jeon and Yang had been fined on charges of assaulting member Seokyu. In June, Ki-O presumably left the group. Around October, Sangyun, Hayoung, Kunhee and Jinu also left the group and IT Entertainment had to recruit new members: Suhyun, Minyeop and...
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