On 4 September 2008, Wooyoung debuted as part of 2PM in their first single "10 Points out of 10 Points" (Korean: "10점 만점에 10점") from their single album "Hottest Time of the Day". They have released five studio albums in Korea and four studio albums in Japan.
On May 24, 2012 it was revealed that Wooyoung will release solo album in early July. On June 28, he performed the title track "Sexy Lady" at the Mnet 20's Choice awards. His first solo mini-album 23, Male, Single was released on July 8  and included two self-composed songs by fellow 2PM members, Junho and Jun. K. In September 2012, Wooyoung, along with JY Park, Taecyeon and miss A's Suzy, promoted the clothing line Reebok's Classic Campaign with a collaboration song named "Classic". On June 9, 2014, Wooyoung released two duets: "Two Hands Clasped" with Park Se-young, and "Fireflies' Glow" with lel. On March 4, 2015, he made a solo debut in Japan with the single R.O.S.E, preceded by a tour of concerts in Tokyo, Osaka, and Aichi in February. He released music videos for tracks "R.O.S.E" and "Happy Birthday", and, in April, the music video for the Korean version of "R.O.S.E".
Wooyoung debuted as an actor in the 2011 KBS drama series Dream High, in which he played the role of Jason, a Korean-American. His performance in the drama made him famous for the English line "Is it my turn already?"; he had help from fellow 2PM member Taecyeon and Nichkhun with his English due to their both being experienced in the language. After his drama debut in Dream High, Wooyoung expressed a desire to continue acting while maintaining a musical career. A representative for JYP Entertainment noted the future opportunities, saying "We're planning to continue Wooyoung's acting career when he receives another great project. He was worried before Dream High began filming, and often wondered whether he'd be able to act, but we believe that he's gained a lot of confidence since then. He's gotten very interested in the acting field, so we plan to continue his acting career, along with fellow member Taecyeon's."
In September 2011, Wooyoung and Dream High co-star Suzy made a cameo appearance in the KBS Drama Special Human Casino. The two idols played the role of a couple caught up in gambling scandals. Their scene wasn't a part of the actual drama, but were rather featured towards the end with the rolling credits. The producer stated "I told these two that I was starting a new project and they told me they wanted to visit, so I thought of giving them a small cameo role."
In 2011, Taecyeon and Wooyoung modeled for the fall collection of the clothing brand Evisu, and in 2012 afor the spring-summer collection. In September he modeled for Reebok's Classic Campaign. In August 2014, Wooyoung was announced as new face of Recipe Cosmetics.