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His portrayal of a start-up investor with a tragic past was well-received by viewers and garnered him a nomination for the Baeksang Arts Award for Best Supporting Actor – Television. Kim returned to the small screen in October 2020 through the tvN drama Start-Up. 2020–2021: Breakthrough and mainstream success In his final project of 2019, he appeared in the play Memory in dream. On November 5, Kim joined the cast in fourth season of the KBS2 reality show 2 Days & 1 Night he received the Rookie Award at the 2020 KBS Entertainment Awards for his work on the show. In October the same year, he starred in the tvN investigative crime drama Catch the Ghost opposite veteran actress Moon Geun-young, in his first leading role in a full-length series. In March 2019, Kim played an aspiring singer in the JTBC comedy Welcome to Waikiki 2.
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In September that year, Kim joined Salt Entertainment after the expiration of his contract with his former theatre company.
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He also starred in the historical drama 100 Days My Prince, which became one of the highest-rated series in Korean cable television history. In 2018, Kim portrayed the lead role of an artist in the drama special You Drive Me Crazy, which had a four-episode broadcast in May. While the drama was still airing, he reprised his role onstage as Valentin in Kiss of the Spider Woman. Later in 2017, he starred in the action comedy Two Cops as a sly conman, which earned him two awards at the 2017 MBC Drama Awards. Kim's next project Strongest Deliveryman, for which he initially auditioned for a supporting role, marked his first appearance in a main role onscreen. Kim made his screen debut at the beginning of 2017 in the KBS2 office drama Good Manager, after auditioning at the suggestion of producer Lee Eun-jin who watched his performance in the play Closer. Later, he expanded his repertoire with darker roles, and gained critical recognition in works such as True West and Kiss of the Spider Woman in 2015, and Closer in 2016. He found minor success appearing in the popular Daehakro (comparable to Off-Broadway) plays Rooftop House Cat and Goal of Love, which were both romantic comedies. His first stage role was in New Boeing Boeing (an adaptation of the French play of the same name) in 2009, which he reprised in 2013. While in college, he joined a theatre group and began acting in plays.