On October 10, 2016, Wooseok made his debut as a member of PENTAGON with the release of their debut album Pentagon. On March 11, 2019, Wooseok debuted in the unit duo Wooseok X Kuanlin with his then fellow Cube labelmate Kuanlin. They released their debut mini album 9801 and seemingly disbanded when Kuanlin terminated his contract.
On October 9, 2023, Cube announced that Wooseok had ended his exclusive contract with them, along with 4 other members of PENTAGON. On January 2, 2024, it was announced that Wooseok had signed an exclusive contract with UNDFND Entertainment as a soloist. On February 15, 2024, Wooseok announced that he will make his solo debut on February 24 with the digital single "Empty Paper".
On March 18, 2025, S27M Entertainment announced that they had signed a contract with Wooseok for his acting activities. On June 16, 2025, it was announced that Wooseok, along with Lacuna guitarist Jung Min Hyuk and SURL drummer Oh Myeongsuk, had come together to form a new band KIK, set to release their self-titled debut EP KIK on June 30. On September 23, 2025, he was introduced as a contestant on the Mnet's band survival show STEAL HEART CLUB.
On December 9, he was eliminated in episode 8.
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