Purpose: The present study investigates human behavioral and emotional experiences based on human-built environment interaction with a specific interest in urban graffiti displaying fear and pleasure-inducing facial expressions. Regarding human behavioral and emotional experience, two questions are asked for the outcome of human responses and two hypotheses are formulated. H1 is based on the behavioral experience and posits that the urban graffiti displaying fear and pleasure-inducing facial expressions elicit specified behavioral fear and pleasure responses. H2 is based on emotional experience and states that the urban graffiti displaying fear and pleasure-inducing facial expressions elicit specified emotional fear and pleasure responses. Design/methodology/approach: The research design is developed as a multi-method approach, applying a lab-based experimental strategy (N:39). The research equipment includes a mobile electroencephalogram (EEG) and a Virtual Reality (VR) headset. The behavioral and emotional human responses concerning the representational features of urban graffiti are assessed objectively by measuring physiological variables, EEG signals and subjectively by behavioral variables, systematic behavioral observation and self-report variables, Self-assessment Manikin (SAM) questionnaire. Additionally, correlational analyses between behavioral and emotional results are performed. Findings: The findings of behavioral and emotional evaluations and correlational results show that specialized fear and pleasure response patterns occur due to the affective characteristics of the urban graffiti's representational features, supporting our hypotheses. As a result, the characteristics of behavioral fear and pleasure response and emotional fear and pleasure response are identified. Originality/value: The present paper contributes to the literature on human-built environment interactions by using physiological, behavioral and self-report measurements as indicators of human behavioral and emotional experiences. Additionally, the literature on urban graffiti is expanded by studying the representational features of urban graffiti as a parameter of investigating human experience in the built environment.