The replacement of medical professions by artificial intelligence (AI) is a current threat in the future as many studies report that Convolutional Neural Networks (CNNs) trained with different databases can overcome the ability of a skin expert to diagnose skin cancer. Those results, however, seem to be affected by the controlled study settings and do not represent real-life experiences. The collaboration between AI and dermatologists seems to form the dermatology future, with both advantages and disadvantages being part of this interplay. On the one hand, dermatologists would gain time and improve patient care through rapid AI-promoted checks and monitoring and better disease inspection. On the other hand, AI can lead to misinterpretations when vague inputs are used and devalue the dermatologist’s expertise in general in case the diagnosis is mainly based on the AI score result. Also, the exploitation of AI dermatology systems by companies that do not hire dermatologists to check the results may have an economic impact on the occupation of the skin expert and cause patient malpractice. We asked a dermatologist, a law expert, a bioengineer, and AI to express their opinion on the following question: Can artificial intelligence replace dermatologists? They all concluded that the absolute replacement is not feasible due to practical, ethical, and legal parameters; however, further regulations are needed to control this AI integration. Has the machine vs. human comparison begun? Yes, but to what extent would it progress?