The landscape of human memory and event cognition research has witnessed a transformative journey toward the use of naturalistic contexts and tasks. In this review, we track this progression from abrupt, artificial stimuli used in extensively controlled laboratory experiments to more naturalistic tasks and stimuli that present a more faithful representation of the real world. We argue that in order to improve ecological validity, naturalistic study designs must consider the complexity of the cognitive phenomenon being studied. Then, we review the current state of "naturalistic" event segmentation studies and critically assess frequently employed movie stimuli. We evaluate recently developed tools like lifelogging and other extended reality technologies to help address the challenges we identified with existing naturalistic approaches. We conclude by offering some guidelines that can be used to design ecologically valid cognitive neuroscience studies of memory and event cognition.