Jung Woo made his acting debut in 2006 and began his career appearing in minor roles on film and television. He drew attention in 2008 for his turn as a morally challenged but lovable villain in action film Spare, the directorial debut of Lee Seong Han. In 2009, Lee directed Jung Woo again, this time in the leading role in Wish, a film which Jung Woo had written himself based on his own experiences as a troubled youth dreaming of becoming the number one fighter at his school. The character uses his real name Kim Jung Guk and nickname Jjianggu, the movie was shot at his childhood home, and high school, Busan Commercial High School, and Jung Woo's real-life friends play themselves in the film. Spanning the years from Jjianggu's school life to his father's last days, the film was an official selection at the 2009 Busan International Film Festival. Jung Woo was praised for his performance and won Best New Actor at the prestigious Grand Bell Awards in 2010. In 2013, Jung Woo played a supporting role as a baker who falls for a divorced single mother in the family drama You're the Best, Lee Soon Shin. His mainstream popularity further increased when he was cast as one of the main characters of Reply 1994, a cable drama about a group of young students from different regions in Korea living together in a boarding house while going to college in 1990s Seoul. This was followed by a role in arthouse spy movie Red Family, produced by Kim Ki Duk. Jung Woo next starred in the 2014 musical biopic C'est si bon. Set in the eponymous live music cafe in Mugyo-dong, downtown Seoul, the film depicts the formation of legendary folk music group Twin Folio, which was active from the 1960s to 80s. Jung Woo previously dated fashion designer Kim Jin. In November of 2013, it was reported that Jung Woo and his co-star in the movie "Red Family", Kim Yoo Mi, have been dating for three months. On January 13, 2016, his agency, FNC Entertainment announced that the couple was getting married on Janua Watch drama online for free.