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Cho himself also dreamed of becoming a musical actor from an early age, however in 1999 while a student at Dankook University he was persuaded to join auditions for Im Kwon-taek's film Chunhyang, and he ended up winning the part from among a field of 1,000 actors.
Chunhyang would screen as the first Korean film in competition at Cannes, although domestically it failed to attract much of an audience.
He is best known for his leading roles in the films The Classic (2003), Marathon (2005), Tazza: The High Rollers (2006) and Inside Men (2015) as well as in the stage musicals Jekyll & Hyde, Hedwig and the Angry Inch and Man of La Mancha.
He is also known for his leading roles in television dramas The King's Doctor (2012), Stranger (2017) and Life (2018).
In 2006 Kwon filed a complaint against Kim Tae-chon, the godfather of Beomseobangpa (one of Korea's three major criminal gangs), for threatening him when the actor failed to keep his promise to hold a fan meeting in Japan.
Things took a turn for the better in 2010 with the box-office success of Korean War film 71: Into the Fire which Kwon reportedly did not hesitate to take on, though he again portrayed a high school student.This was followed by appearances in My Good Partner, the world's first movie made for mobile phones, and the music video collection Project X.His next film released in early 2004 was also a hit.Based on an original story by webcomic artist Kang Full, Pained was directed by Kwak Kyung-taek in a departure from his previous macho movies.Kwak said, "The production company told me Kwon Sang-woo was contemplating the part, and I said I would do it only if Kwon does.