This was why, despite very few actual legislative accomplishments, Obama’s presidency always felt more relevant in the moment than perhaps it actually was. It was so intertwined with the same faces in our culture that we see on magazine stands, album covers, movie screens and sitcoms. Obama always felt fresh and cool among the Hollywood elite, despite his party being decimated out from underneath him in consecutive congressional wave elections.

Obama and his administration wanted to be as much a part of Hollywood as Hollywood wanted to be a part of him. This was his chosen path to push his agenda — through the people in culture with the loudest microphones whom he felt could influence the largest number of people to fall in line with his ideas.

Hillary Clinton tried to mimic this same strategy with her campaign, enlisting athletes, TV stars and pop stars to help drag her over the finish line.