The essay aims at discussing visual arts and gender issues, with specific reference to models for female empowerment by means of aesthetic paradigm shifts. These took place thanks to pioneering video artists in the 1990s and were then upheld by new millennium music pop stars in highly influential videoclips. I argue that videos by artists such as Pipilotti Rist, Cheryl Donegan, Mona Hatoum, Andrea Fraser, and Susan Hiller matter today for how they tackled gender issues by means of the moving image, especially by challenging the male gaze and creating gender specific perspectives long before women could claim a similar influence on the television business and in the movie industry. They offered ground-breaking strategies in visual representation and video narratives of considerable impact since they were later adopted in public life, particularly through female pop stars’ aesthetic transfer into music videoclips, such as with Beyoncé. In this regard, I observe how art historical references are applied in recent videoclips to challenge the male gaze, letting a threefold strategy emerge: thematic reprise, iconographic substitution, and aesthetic transposition.