Early career and breakthrough
Jung passed the KBS actors' audition, and was soon signed by leading talent agency SidusHQ. Along with four other newcomers from the agency, he made his acting debut in 5 Stars, a mobile drama produced by SidusHQ and broadcast over SK Telecom. A few minor roles on KBS followed.
Jung's first major break came in the 2004 melodrama series I'm Sorry, I Love You, playing the supporting role of an actor who belatedly falls for his childhood friend (Im Soo-jung) and who has an unusually close relationship with his mother. The series was a critical and commercial hit. Following the conclusion of this series, Jung was cast in two films in 2005: All for Love, and When Romance Meets Destiny.
After playing his first leading film role in Gangster High (2006), Jung returned to television in the well-received action drama Time Between Dog and Wolf (2007), in which he and Lee Joon-gi played NIS agents. His portrayal of a policeman who unknowingly becomes interested in an autistic young woman (Kang Hye-jung) in the film Herb netted him a Best New Actor award at the Chunsa Film Art Awards. Jung then played a 1980s-era college student tutoring a high school girl (Cha Soo-yeon) in surreal romance For Eternal Hearts, which was the opening film for the 2007 Puchon International Fantastic Film Festival.
Director Lee Joon-ik then cast Jung in Sunny (2008) as a double bassist in a "consolatory band" who helps the heroine (Soo Ae) find her husband during the Vietnam War. The year after, he played a fugitive who faces off against a small town detective (Kim Yoon-seok) in Running Turtle (2009).
For his first role in a historical drama, Jung played a Goguryeo prince torn between love and duty in Ja Myung Go (2009), based on the folktale Prince Hodong and the Princess of Nakrang. Although Ja Myung Go received lackluster ratings, Jung bounced back with a leading role in the popular family drama Smile, You, starring alongside Lee Min-jung. Of playing an endearing "beta male," Jung said, "I am glad to be able to play a fun character and work on a fun script."
Later in 2010, Jung appeared in a one-act Drama Special episode, The Great Gye Choon-bin, playing an art therapist who overcomes his fear of the dark through his relationship with a kindergarten teacher.