In this world of different people with diverse talents and abilities, being cool could mean different things. Usually, this relies heavily on personal judgment and the interests of an individual. For instance, I chose Dave Chappelle, the American Comedian, as one of the coolest guys I have lived to know because comedy has always appealed to me. In this text, I will compare and contrast Dave Chappelle with yet another great figure, James Longley. I will look at the major similarities that are shared by the two and also point out the differences that exist between them. James Longley is a filmmaker who was named one of the MacArthur Fellows in the year 2009. He has a rare taste for direct experiences and this is what has often set him on his heels to distant lands in such of primary information. Longley is known to have spent lengthy periods of time in foreign countries such as Iran, Russia, and Iraq. The most amazing part of it is that he has managed to survive in one of the world’s most dangerous combat zones without any security as a foreigner. This is among the aspects that saw him be nominated for the Oscar awards as an outstanding documentary-maker. One clear similarity between Dave Chappelle and James Longley is their humble nature. Both the two persons lack the usual sense of importance that is common among today’s American celebrities. Instead of walking around equally prominent people of their caliber and driving big cars, they have this habit of intermingling with ordinary people who greatly appreciate this. While Dave Chappelle is having a cup of coffee in a local coffee shop upcountry, James Longley is busy talking to the locals in war-torn Iraq. However simple it may appear, this act has touched the hearts of many people who have had the chance to chat with this two. It is not a normal thing to come across an American celebrity, and what’s more, a millionaire, strolling down narrow streets in the company of low class guys and not wanting to show that he’s got more cash and a big name than they’ve got. Another similarity that stands to be observed between the two big names is their possession of self-control. Both the two have had to make important decisions in their lives, and mostly about their careers, on their own without the influence of another party. Dave Chappelle walked away from his fifty million dollar contact on his own choice against the wish of his fans and the owners of Comedy Central . I am sure that had Dave sort for advice from anyone on the issue, no single soul could have told him to walk away and leave behind such a pretty amount of money. On the other hand, James Longley made his personal decision to make films on the challenging conditions that faced other people in atmospheres such as war as was the case with Iraq. Few or no documentary-writer will be willing to leave the beauty and comfort of peaceful America to make a documentary in a risky environment (Dunn par. 4). The third similarity between Dave and James is the fact that they give the audience something new to watch and talk about. They are both creative. They have decided to break away the monotony that comes with watching certain movies and soaps. That is why Dave made it big with his comedic portrayal of American pop culture and prominent racial stereotypes. This was something that had never been