He debuted as a member of the South Korean boy group Pentagon in October 2016 and also formed a duo with Lai Kuan-lin as Wooseok X Kuanlin in March 2019, under Cube Entertainment.

[4] In 2017, Wooseok co-wrote the Produce 101 Season 2 hit song "Never" and Wanna One's debut title track, "Energetic" together with Pentagon's leader Hui.

[10][11] On February 22, 2019, Cube Entertainment announced that Wooseok would be debuting in a new unit project alongside labelmate and former Wanna One member Lai Kuan-lin.

[20] In February, he starred in the web drama Nickname Pine Leaf for the SBS YouTube channel yogurD, where he plays two different versions of himself: PD Jung Seok-woo and Pentagon's Wooseok.

[24] On October 9, it was announced that Wooseok had left Cube Entertainment alongside fellow Pentagon members Yeo One, Yan An, Yuto, and Kino.

[26][full citation needed] On January 2, 2024, Wooseok signed an exclusive contract with UNDFND Entertainment, and announced an album and fan meeting within the first half of the year.