10 Dave Chappelle Quotes To Live By
Back in the summer of 2014, my mom gave my older cousin Eric and I tickets to see Dave Chappelle at Radio City Music Hall in New York City. We got up early that day, hopped the train from Newark into Penn Station and walked all the way to 50th Street and 6th Ave. My cousin Eric is this old school Rasta, so we smoked the whole way and talked about life. The show ended up being Chappelle’s formal, big return to comedy after he quit Chappelle’s Show and took a hiatus from fame. As someone that grew up watching his show and stand up specials on Comedy Central, that night will always be a very special memory of mine. I still own the t-shirt I bought that night that says “I was there”, as if Chappelle knew even then that despite his recent career setbacks, he was destined for great things.
Why and how Dave Chappelle left his job with Comedy Central has always been a strange topic, but one thing is for sure – there is something incredibly respectable about it. Most people would do pretty much anything to achieve the fame and wealth he was on a steady track to receive, but something in him told him it wasn’t right. I imagine that leaving the show mid-way through the production of the third season of his show was probably the most difficult decision he has ever had to make in regards to his career, and it was a decision that came very close to destroying it. With what seems like a ravenous level of determination and a pure love for comedy as an art, he has managed to rise above the hate and criticism and become one of the greatest comedians alive today. The past few years his specials and SNL appearances have received numerous Emmy and Grammy awards, and most recently he was given the prestigious Mark Twain Prize for American Humor.

His stand up and specials have gotten a lot more mature, introspective and full of wisdom in the years since his return. In this article, I’ll present a few quotes from him that I think possess something insightful for anyone to take and apply to their everyday life. So kick back, puff one, and lets get our meditation on.
You got to be careful of the company you keep.
Like most of the quotes on this list, this one is pretty straightforward and to the point. It’s probably something you’ve already heard or read before but sometimes in life it can be really easy to forget to put it into practice. When you are surrounded by people that are miserable or just down on their luck, they have a tendency to bring you down with them. Usually it’s not intentional because it can get lonely on the bottom. But you should always strive to surround yourself with like minded people, or those that embody the character qualities you find most admirable. When you surround yourself with uplifting people, you tend to feel more uplifted.
The world can’t tell you who you are. You’ve just got to figure out who you are and be there, for better or worse.
Another pearl of wisdom that so many of us take for granted – ALWAYS be true to yourself. So much of life is other people or aspects of society trying to pigeonhole you into playing a specific role. But what if that role they are pushing on you is counter to who you truly are? If you march to the beat of the drums of others, you’ll never find solace in life. You will simply always be chasing after something that was never really there. But when you are true to yourself, even when there is criticism and opposition, no one can take that from you. It is self empowerment at its finest.
When I’m on stage, I get real happy there. Maybe that’s the only time in my adult life I feel like myself.
This quote goes hand in hand with the last one and speaks volumes about Dave Chappelle as an entertainer. He always comes off as so humble about his fame, so much so that it’s inspiring to watch him perform. He seems to have found his passion in stand up comedy and it shows. If you want to have as much fun doing what you do as he does doing comedy, you HAVE to seek out that which makes you feel complete and go after it like there’s no tomorrow.

My father told me ‘Name your price in the beginning. If it ever gets more expensive than the price you name, get out of there.’
This is one that I haven’t thought enough about in life, and it really spoke to me when I read it. I think by ‘name your price’ he’s really talking about what you are willing to do and how far you are willing to go for something you love. When the stakes get to high, it might be time to dip out. I can’t help but think that maybe this was his line of thinking when he decided to leave Chappelle’s Show. I also want to add to this quote that it’s also good to know and be aware of your value, so you never make the mistake of selling yourself short.
Constantly take inventory of what’s important to you.
This is such an extremely important point delivered in such a simple package. If you ever lose sight of the people and things that you love and care about, you run the risk of losing them. I’ve been guilty of taking for granted close friends, families and relationships that ran their course simply because I failed to recognize everyday not only that they are important to me, but WHY they are. Make a habit of taking inventory everyday of that which matters and you can avoid a life full of regret.
One of the things that happens when people make the leap from a certain amount of money to tens of millions of dollars is that the people around you dramatically change.
Cash rules everything around us… well, almost. There are so many people that chase fame and wealth their entire lives, but just like Dave Chappelle pointed out in the beginning of his Netflix special Sticks and Stones, even Anthony Bordain killed himself. As dark as that is, the point is to recognize that there is so much more to life, and that fame and wealth we are all chasing might be a bit of an illusion.

You’ve got to say ‘yes’ to your destiny. Life’s happening right now, look around you. There goes some life. Come on, Mamma, live!
Whether you decide to stay still, petrified by your own insecurities and second guessing everything, or you decide to go hard at everything you do, life goes on, with or without you. So why not give it your all? I know, this can be easier said then done and I’m admittingly being a bit of a hypocrite, but at the end of the day, it should always make the most sense for you to do your best to take hold of your destiny. It’s like that quote from the book Fight Club – “This is your life, and it’s ending one moment at a time.”
Something about New York, man: You can do more comedy there probably than you can anywhere in the world. If you’re interested in being funny, New York is the place to go.
Ask yourself honestly – are you doing EVERYTHING you possibly can to get what you want out of life? I ask myself this a lot because the answer tends to be no, yet I catch myself complaining about my circumstances and the end result so much. But if you can take a step back and recognize there is more you can do, then you can hit the brakes and maybe rehash a new game plan. Chappelle moved to NYC in the 80s to chase his dream of being in comedy. Why? Because NYC is where it’s at. Not that he couldn’t make it anywhere else, but he knew that that was the place he needed to be to make his dreams happen. You need to figure out what your NYC is and go after it before this life passes you by.
You know, [to] be able to do something great in your life, you’re gonna have to realize your failures. You’re gonna have to embrace them and figure out how to overcome it.
It’s ok to fail. As a matter of fact, it is inevitable. You can’t avoid the fact that sometimes you will swing and miss, but the ability to study why you failed is something we all need to succeed. In studying and, as Dave Chappelle put it, realizing your failures you can and will get better at your craft. It is essential to becoming a master at anything, and that includes simply being able to handle the trials and tribulations of everyday life.

Hey hey hey, smoke weed every day.
I know, this doesn’t seem like the best pearl of wisdom to end on, but I think it embodies what I admire most about Dave Chappelle – he always seems to be having fun. Whether it’s watching him on stage or in a movie, I always get the impression that no matter what he does his heart is in it. There is such a beauty to that and I feel incredibly lucky to have grown up watching him and being influenced by his comedy.