As technology developed, more avenues for people to share the design grew compared to the traditional ways of sharing. Now design is everywhere. So what makes designs stand out from the rest? This research paper focuses on meaningful designs that were able to stand the test of time. Looking through the history of graphic design, design evolved as a traditional media to an online media form which opened up a community of designers who were once separated. Particularly focusing on iconic American and Japanese graphic designers and their styles and their perspective on creating meaningful design. As a deliverable, the project was set up as design challenges on a social media platform, Instagram, where the challenge was to create something meaningful with limited materials and random choices and theme idea selected by the audience. By collecting data of engagement, it will identify what kind of graphic design makes audience engagement and recall.