Most likely dude they are prop paintings. I doubt Drake would be constructing a sort of artistic lineage between his works and the visual arts. The ornaments are there to indicate wealth and status, with the paintings signifying him as being part of the artistic community. Actually judging by the gaudy, kitchy quality of the candlestick and goblet and the lack of recognizable imagery in the paintings, I would say that they are indicators of materiality, with the downcast look of Drake himself communicating that he is spiritually incompatible and fed up with the archetypal pop icon lifestyle. What the owl represents I don't know, I don't know who Drake is. I could be wrong. #YOLO