Notes From A Comedy Junkie: Hanging With Dave Chappelle and Donnell Rawlings: Strumming Our Pain and Still Finding the Funny After 30 Years in Comedy 

Sara Dahms is a comedy superfan who even goes so far as to call herself a comedy nerd. Raised on National Lampoon, John Hughes, Gene Wilder, and Fairy Tale Theatre, her life changed after her older sister showed her Eddie Murphy’s Raw in 1988. Soon after, she found  and became a stand-up junkie for life. Eighteen months ago, she took her first comedycation to see Jeff Ross play in Miami on her birthday.  Since then, she’s been traveling all over the country checking out the best comedy everywhere, a confirmed comedy addict, and now she’s agreed to share her travels with us. This is her column. In this edition, Sara heads back to New York City to see Dave Chappelle in Residence at Radio City Music Hall.

Read Notes From a Comedy Junkie Vol 1 here, check out Volume 2 here, and read more about her travels with Volume 3 (Chicago), Volume 4 (St. Louis), Volume 5 (Moontower),  Volume 6 (Los Angeles), Volume 7: Colossal Clusterfest and The Comedy Store, and Volume 8: Just for Laughs 35.


Donnell Rawlings is a really fun hang and super nice guy so needless to say, I was very happy when I ran into him at Just For Laughs in Montreal a few weeks ago. He and I got into a pretty deep conversation about life and comedy on my last night at the festival. I love a genesis story, so I asked him how he got his start in comedy. His answer took me completely by surprise… He was in the audience at a show in D.C. and he started heckling the comic who was on stage. Donnell’s jokes destroyed the room. He was so funny that people actually came up to him after the show wanting to know if he was a plant and asking where they could see him perform. Donnell made it perfectly clear to me that in hindsight, he believes that heckling is a “cowardly type of comedy” and that the only reason he was doing it was because something inside of him was calling him to the stage but he didn’t have the courage to get up there yet. I’ve heard a lot of genesis stories in my day, but this one is definitely an original. It was getting late and he and his friends were leaving to get something to eat. I was tired so we said our goodbyes but before they left something amazing happened…. Donnell invited me to Radio City Music Hall to catch one of the shows Dave Chappelle is putting on during his month long residency at the historic venue…. Um, what?!?! Come again?!? Wild horses couldn’t stop me! True to his word, Donnell  Rawlings texted me a few days later with the date that worked best for his schedule. I booked my trip to New York that afternoon.

I’m about to head out to Radio City Music Hall, but I have no idea how much fun I’m about to have!

The day of this colossal comedycation finally arrived. I had seen pictures from all of the sick lineups and amazing hangs that were being posted onto social media and they were definitely adding to my excitement. You see, this run of shows is very special. The final show of his residency at Radio City Music Hall will be on August 24th, his 44th birthday, which also marks his 30th anniversary of being in comedy. It’s a really significant celebration and being able to be a part of it, in any way, means a great deal to me. That being said, I still didn’t quite know what to expect from this adventure. I went into it thinking, “I’ll see Chappelle and then go to The Comedy Cellar to catch a late show.” I didn’t want to get my hopes up and I certainly didn’t expect anything more than that to happen…. I arrived at Radio City and waiting for me in the box office was a ticket AND an after show guest pass!!!! I was so excited that I probably looked like a crazy person with the size of the smile I had on my face. Comedy fills my cup and in that moment, “my cup runneth over!”

This particular evening was being hosted by the super funny Wil Sylvince and featured four cast members from “Saturday Night Live.” Pete Davidson cracked me up with his jokes about how he would or would not dress if he had no arms, Colin Jost told a hilarious story about a “chocolate incident” he had while at Just For Laughs, Leslie Jones’ energy and story about being at a party with Prince were amazing, but Michael Che’s Marco story took the cake. Most stories that comedians tell seem to have one punchline that comes at the very end but I swear it felt like this story had about 10 of them. I loved how one of his first big laughs of the story came from a simple look he gave with his eyes. Che is obviously a very talented writer and has mastered the art of delicately peppering thoughtful, social commentary throughout his act. I hope to hear or read more of what he has to say in the future.

Donnell Rawlings, Pete Davidson, Leslie Jones, Colin Jost, Wil Sylvince, Michael Che and Dave Chappelle

Now, for the moment we’ve all been waiting for…. Dave Chappelle!!!

Dave Chappelle is in a category of comedians that I affectionately refer to as the “pontificators.” It’s the highest level of skill a comedian can attain in my opinion.  Dave is a prolific speaker and a performer with a message. When you go to a Dave Chappelle show, he’s going to do much more than simply make you laugh. He’s going to make you think. He’s going to make you feel. He’s going to point out hypocrisy in the world around us. He’s going to challenge you to laugh at yourself and the mainstream popular culture. This type of comedy is not for everyone. Chappelle addressed his critics by saying that “some peoples’ ears just aren’t calibrated for comedy the way they used to be.” I definitely believe that there is truth to that. I also believe that it’s great to be in tune with your brand of funny and if Dave Chappelle’s jokes insult you, there is enough comedic talent out there for you to find your niche and keep it moving. His jokes did not promote discrimination or incite hate. Comedy is his method of addressing tragedy and promoting healing…. There is no denying the interconnectedness between comedy and tragedy. Too many people are hurting and holding their pain inside or turning to unhealthy means to release their suffering, while laughter is the best medicine.

Comedy IS an amazingly, healthy release. By taking on very delicate subject matters such as race, gender, sexuality, oppression and politics Dave Chappelle honed in on all of his pain, all of our pain, all of the pain of our nation, channeled the tragedy, turned it into comedy and set it free.

After the show I met up with Donnell and we headed off to the first of two after parties. The first one took place at the venue. There, I had the pleasure of officially meeting Barry Katz. I had seen him in passing the past two years at JFL but never actually met him. The man gives off the most positive vibes ever! It’s no wonder everyone loves him so much. This party was very chill. Everyone kind of hung out in cliques and talked. I met a couple of Donnell’s friends, Forty and Andy and we had an amazing conversation about comedy. Ever since Donnell and I spoke about his start as a heckler at JFL, I kept wondering when it was that he finally took the leap from heckler to stand-up so, I asked him. His “first time” on stage was at Comedy Connections in D.C..  Mike Washington introduced him and that night completely changed the trajectory of the rest of his life. Donnell was hooked. Being up there, making people laugh felt good, really good and he got laughs, big ones. The word about the hilarious new guy on the scene quickly spread throughout D.C. and he started booking shows left and right. I asked if his super quick success affected the way veterans treated him and he said “absolutely.” They would say, “Sure he’s funny, but he ain’t got no time.” So, he would work at it, and work at it and then come back and kill for 20 minutes. Then they’d say, “Yeah, he’s got time but he doesn’t have enough material. He does too much crowd work.” Donnell took their criticism and turned it into the feedback he needed to perfect his set. He came back with 20 minutes of solid gold material. Once he had his 20 minutes perfected, he felt ready to take it to the next level. He wanted to be on “Def Comedy Jam.” He came up with a hilarious yet effective strategy to get himself on. He knew that the co-executive producer & main talent booker, Bob Summer, worked at Rush Communications. Donnell called the company and somehow reached Bob’s secretary.  He then acted as if he and Bob Summer went way back. When his secretary answered the phone he simply said, “Hey, where’s Bob at?” With little more than that she put him through and Bob picked up the line. He must have liked what Donnell had to say because he ended up telling him to come out and play The Peppermint Lounge. Donnell let me know that, “if you could rip ‘The Peppermint,’ then you could work ‘Def Jam.” I was amazed that this strategy actually worked! Good for him for having the guts to try. Four minutes into his act at The Peppermint Lounge actor/comedian Royale Watkins told Donnell from the side of the stage that he had gotten “Def Jam.” Bob Summer loved him. Right then and there, only four minutes into his act, Donnell said “goodnight” and walked off stage. His work there was done and he was not going to let anything go wrong. I asked him if he got “The Chappelle Show” from doing “Def Comedy Jam” and he said “No.” That was a different story all together. Donnell would often do spots at Barry Katz’s the Boston Comedy Club and there he and the young door guy, named Neal would cross paths a lot and they always got along. This door guy was none other than the great Neal Brennan. Neal had also worked as a P.A. on the show “In Living Color” and during that time he wrote a short film that he wanted to direct. With the tone of a proud parent Donnell stated, “The first thing Neal ever directed was me.” Rawlings figured that as a P.A./door guy Brennan probably didn’t have the money to pay him for the job, so he doubled down and basically took stock options on Neal’s talent instead of a paycheck. He told Neal not to worry about paying him and just, “Throw me a bone when you can.” That “bone” turned out to be a little show that Neal co-created and wrote called, “The Chappelle Show.” Neal Brennan and Dave Chappelle went on to cast Donnell Rawlings in 22 out of the 33 episodes that aired from 2003-2006!!! My mind was blown and with perfect timing, in walked Dave Chappelle!!! He floated around the room, talked and hung out with his guests of SNL stars, business executives, and artists like any good host would. Donnell introduced me to him. I shook his hand and said, “happy 30 year anniversary!” I still need someone to pinch me to prove I wasn’t dreaming.

Wil Sylvince and me at the after party

Not too long after that Donnell and our crew headed to after party number two. This one was located at a trendy Manhattan night club and we needed to use a secret Chappelle guest password to get in. We were escorted in by a security guard and taken behind the velvet ropes of the V.I.P. section. Wil Sylvince and all of Dave’s SNL guests were already there when we arrived. All of Dave Chappelle’s crew were extremely open and friendly. I only knew a handful of people there, but it certainly didn’t feel like it. The young, the old, the male, the female, the rich, the famous, everyone was cool. I had SO much fun! This party was my kind of party!!! The waitresses kept the bottles popping, the D.J. kept the music bumping and our generous host, Dave Chappelle kept us turned up by dancing and singing along side his guests all night long. I danced until 3:00 in the morning, then ended my night in my traditional New York way. With a Reuben sandwich at Sarge’s Deli. Life doesn’t get any better than this!

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Sara Dahms

Sarah Dahms is a comedy superfan hails from Chicago and travels all over the country checking out the best comedy everywhere.
Sara Dahms
Sara Dahms
Sarah Dahms is a comedy superfan hails from Chicago and travels all over the country checking out the best comedy everywhere.