This comparison of Trump and Reagan is not meant to be viewed as either a positive or negative, but a reflection of our current society and culture.
One reason Trump won the election is lot like how Reagan won. Reagan was an actor and when he ran for president he did it almost like he was in a movie. The country needed a strong president. They needed a president that was like something out of the movies. He was at the time exactly what people imagined as the prefect president. It was the greatest acting job ever, because he made people believe in America again.
Today people love reality tv. They want people that seem real and say what they mean. Trump isn't another politician, but instead he is like Gordon Ramsay, John Taffer from Bar Rescue, or Mr. Wonderful from Shark Tank. He is that guy on the reality show that tells off the people you don't like and is the straight shooter. He is that boss you actually like on Undercover Boss. People want to be like Trump. Rich, powerful, married to a hot spouse, and able to say what they want to say.
Voting is not just about making a decision based on logic and reason. It is emotional and people are looking for something in a president that is either thier ideal (Reagan and Obama), someone they like (Bill Clinton and George W Bush), or someone they want to be (JFK or Trump).