There are many artistic support systems available for artists, but none of them provides high-grade collaborative support for traditional artistic painting as an assistant. To collaborate with human artists, the support system should involve essential artistic procedures and be capable of imitating basic artistic techniques of human artists. In this paper, we address this issue and introduce a novel painting support system, namely Skywork-daVinci, based on a human-in-the-loop mechanism. A CPSS-based approach is proposed for collaboration between human artists and machines. Based on the approach, we develop a robotic painting system to imitate painting techniques of artists. Then, an acrylic painting case is presented to demonstrate the feasibility of our system. Furthermore, comparisons between existing robotic painting systems and ours are discussed. As experimental results show, our robotic painting system could imitate the essential painting techniques of human artists and reproduce the paintings drawn by them. This primary system acts as the basis to realize our collaborative artistic support system entirely in future work.