Dane Cook was one of the best comedians when we were in high school, we got tickets and went to see him live. It was awesome and he was hilarious, he burst on the scene in 2003 with his CD/DVD Harmful if Swallowed. The album went platinum and features some of his best work featuring "Umm, Hellllo?", "The BK Lounge", "Slip N' Bleed", "Not So Kool-Aid" and many other classic skits. He then released Retaliation which went double platinum and led to his first HBO special, Dane Cook: Vicious Circle. He hosted Saturday Night Live twice and starred in some pretty good movies, Employee of the Month, Mr. Brooks, Good Luck Chuck, and My Best Friend's Girl. It seemed like he was on top of the world, so what happened? In 2012 Cook made a joke referencing the movie theater shooting in Aurora, CO which really hurt his following (understandably so... not okay). He also has been named by numerous other comedians as someone who steals their jokes and someone they do not find all that funny. He was also popular before the age of YouTube and Social Media which made it more difficult to spread his comedy and interact with fans. In my opinion it seems like he struggled to adapt into other medias, such as podcasting and the other factors really hurt his credibility. 
Another guy I looked at was Kevin Hart, who has been huge for a few years now. After a slow start to his stand up career he began to switch the focus of his stand up and jokes, he started using his own insecurities and life experiences in his routines. Starting in 2009 Hart had a great run with stand up tours; I'm a Grown Little Man (2009), Seriously Funny (2010), Laugh at my Pain (2011), and Let Me Explain (2013). After his last tour in 2013 Hart extended his career by venturing into film and has been a big success. With films like The 40 Year Old Virgin, Death at a Funeral, Little Fockers, Think Like a Man, Ride Along, among a few others. In most of these movies Hart is not the lead role or even the supporting actor, he usually plays a secondary character but he plays them perfectly. You walk out of the movie talking about his role. He has also played alongside some of the biggest actors of this time like Will Ferrell, the Rock, Ice Cube, Ben Stiller, etc. He has also hosted Saturday Night Live a number of times. Hart also benefits by being in the social media age, he is one of the biggest social media stars and has one of the largest followings online. After his stand up "career" Hart is arguably a bigger star now then he was during that time. 
One last comedian I will bring up is Richard Pryor who was popular long before either of the previous two guys I mentioned. Pryor is considered by many to be the greatest stand up comedian of all time, and for good reason (if you have not watched any of his material, I recommend you finish reading this and immediately go to YouTube). He got his start by performing in New York City nightclubs by opening for musical acts and other comedians. In 1966, Pryor started performing on TV, doing his skits on shows like The Ed Sullivan Show, Johnny Carson, and Merv Griffin. After his TV performances he ended up in Vegas opening up for the likes of Bobby Darin, however Pryor was not fond of the rules in Vegas so he went to Hollywood. He starred in a few films, had his own NBC show, and hosted Saturday Night Live during this time. He also began writing for shows like Sanford and Son and worked with Mel Gibson on Blazing Saddles. Pryor was successful in everything he did, from his stand up to his film roles. In 1986, he was diagnosed with multiple sclerosis and even that would not hold him down as he kept performing. Pryor is a prime example of a comedian branching out into other mediums and being extremely successful. He was extremely popular long before the time of social media and is still popular and hilarious now. That is one of the many reason he is considered as the greatest comedian of all time.
In my opinion, Pryor is the greatest comedian of all time and it seems his model is one that Kevin Hart has followed. It is really difficult to solely be a stand up comedian, you have to be able to adapt and explore different avenues if you have to extend you career. Pryor was before the social media age but Hart has used that to catapult his career even higher and Cook missed the boat. Hart is still extremely successful but has moved over to film exclusively and Cook is no where to be seen. Ultimately where Cook failed, Hart excelled. Cook also made a joke in very poor taste and that was a key factor in his down fall. However one of the biggest ways to judge a successful comedian is how well their skits age and all 3 of these are no doubt successful by that measure. You can go on YouTube and pull up any of their skits and still laugh your ass off.
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