A new and distinct cultivar of Caladium plant named ‘;Clowning Around’;, characterized by its intermediate to tall height; upright and mounding plant habit; dense and bushy appearance; vigorous growth habit and rapid growth rate; fancy-type leaves that have dark green-colored margins with greyed red, greyed purple and red-colored centers with random dark green-colored spots and blotches; and leaf petioles that are medium green flushed with greyed red in color with dark greenish brown-colored stippling, streaks and tessellations.