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5 Award-Winning Documentaries on Legendary Comedians

The life of a comedian may seem like a life figured out and full of joyous pomp. But if you dig a little deeper, you’re going to see a lot of psychological issues, a lot of hard work, repetitive toil and frustrating failures behind every comic that makes it to the television screen. Here are five award-winning documentaries that chronicle this amazing profession.

1. “Looking for Lenny”

The documentary “Looking for Lenny” is a controversial exploration of the fear of words and expression. It also looks at limitations that the government and society are beginning to place on freedom of expression in comedy. Lenny Bruce was renowned as the man who pioneered the industry of stand-up comedy. He came into the limelight around the 1950s and was known for his disregard for censorship and hypocrisy which resulted in a target on his back by cultural crusaders that aimed to label his act as obscene. His enemies would be persistent to have law enforcement arrest him so he would stop performing completely. His rebellion became a cultural phenomenon because it broke the social boundaries of a closed-off uptight era, but he paid a high price for it. His life ultimately devolved towards self-destructive behavior, paranoia and ultimately, early death.


2. “Mr. Warmth: The Don Rickles Project”

Bagging 2 Primetime Emmy Awards, this documentary posted at LA’s Victory Studios is all about the legendary performer who traded in social taboos; Don Rickles. whose core group of friends included the Rat Pack and its Chairman of the Board, Frank Sinatra, was successful in charging people money to insult them in some of the most offensive ways possible. His attacks on ethnicity were never off-limits and his audience loved it. In this amazing documentary, we see inside the mind of Rickles as he developed his unique style. Produced by Bob Engleman at Victory Studios, John Landis directed the amazing stories told by A-list celebrities who felt it was an honor to be insulted by Mr. Warmth. Victory Studios provided all the technical support in digital High Definition and exceeded all expectations for theatrical quality, something very important to Director Landis. Victory’s LA facility was the home of the production as it took shape. Don Rickles son worked on the editing at Victory along with other professionals. Victory’s Seattle facility is the largest in the Northwest and leads the country in the development of HD production and post.


3. “Joan Rivers: A Piece of Work”

The documentary on Joan Rivers as she turned 75, A Piece of Work, portrays the amazing history of this extraordinary comedienne. She wasn’t born into the role of criticizing people’s clothing choices, but she learned to use it as one of her comedic themes. Joan Rivers became an idol for female comedians everywhere, and this documentary which won an editing award at the Sundance Film Festival shows us how she did it. Even at that, because she was so prolific and such a hard worker, it’s only a small glimpse of her vast career. From her famous hosting of The Tonight Show to the strange “break-up” with Johnny Carson, this doc does a great job showing Joan’s persistence and passion for hard work right up to the end. This documentary speaks on how show business really works, how gruesome it can be and that it’s not all the glitz and glamour it’s shown as.


4. “American: The Bill Hicks Story”

The light that this counterculture comic brought faded too early because of Hicks’ death from pancreatic cancer in 1994, but his fierce brand of heated satirical rage left a meteoric mark. One could safely call Bill the Lenny Bruce of his time, and his on-stage monologues would sometimes steer into territories that would challenge the audience. This documentary has brilliant animation and a lot of archival footage that serves a wonderfully impactful tribute to a very volatile voice, a voice that allowed us to see distasteful truths about the world at large, alongside a viewpoint on drugs that you might never have considered before.


5. “Comedian”

This documentary is one of Jerry Seinfeld’s first post-sitcom works that shows how his stand-up comedy paved the way to have the network take a chance on him. It not only showcases his skill at creating great shows in small clubs all over the country, but it introduces us to another rising star comedian named Orny Adams to illustrate Seinfeld’s critical work philosophy. Orny’s example of not listening to constructive criticism and a constant focus on what he hasn’t achieved shows Jerry’s audience how the Seinfeld legacy became so successful and powerful. He explains that choosing the life that’s right for you is the key, not hanging on to what’s not possible by constant complaining. This doc’s an informative and intriguing examination of the stages of stand-up comedy and how it remains the same whether you’re an up-and-comer or an established icon. You still have to come up with great material and you have to dish out your hopefully witty jokes to strangers so you can find out what’s working and what’s not.


These five documentaries will make you laugh and inspire you about what it takes to be a successful hard-working stand-up comedian.

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