By now, Guapdad 4000‘s melodic reputation should precede him. While some of his contemporaries are sharing uplifting holiday anthems, however, Guap has chosen a more somber and introspective route with his latest Water Wippin Evan– directed video that finds the singer feeling reflective this holiday season. While Guap’s lyrics are normally filled with punchlines and witty wordplay, “Painful Christmas” is a stark contrast with its lyrical narrative and depth.

Press play on Guap’s latest below.