Howard Stern is an accomplished painter who has created multiple artworks, often focusing on subjects like old, abandoned buildings and natural landscapes. He has painted several covers for Dan's Papers, including a series featuring deteriorating barns and beach scenes such as "Southampton Dune." Stern is drawn to the metaphorical and historical aspects of aged structures, appreciating their natural decay and the stories they evoke. He also enjoys capturing light, shadow, and texture in his work, which he approaches with detailed observation and evolving technique. Stern has expressed pride in his painting skills, despite some skepticism from fans who find it hard to believe he is the artist behind his photorealistic pieces. He has painted portraits of cats as well, including one of his kitten Helen, which his wife Beth turned into a T-shirt to support animal rescue. Stern has shared some of his paintings on social media and has considered exhibiting his work for charity. His painting process often involves taking many photographs of his subjects at different times of day to study light and shadow before creating detailed studies and larger pieces. Stern has been painting for several years and continues to develop his craft, finding joy in drawing and the challenge of capturing intricate details with pencil and paint