Cassandra Dee Will Make You Laugh and Feel Less Alone

Portrait of Cassandra Dee standing outside.
Cassandra Dee Photo: Greg Goldstein

Looking to laugh and feel less alone? Then mark your calendar and come out to Cassandra Dee’s first full-length album recording at Helium Comedy Club on April 10, 2022, at 8:30 p.m. Cassandra Dee’s brand of comedy is dark and self-deprecating, is full of honesty, and tackles subjects like depression, bullying, and suicide. I’ve been a fan since I first saw her perform in the 2017 Philly’s Phunniest preliminary round, a competition held yearly by Helium Comedy Club to determine the funniest stand-up comedian in the city. The comedian’s jokes were so original,  and vulnerable, she stood out effortlessly in a group of close to 20 comedians competing. 

She won the entire competition the following year. 

Given how much time I spend watching others and performing on stage myself, I don’t always, or ever, remember the exact moment I first meet or see any specific comedian. Time tends to blur. But, I remember the exact moment I saw Cassandra Deeand I’ve been following her ever since.  

Cassandra Dee can be heard on SiriusXM radio, has hosted shows like “Really Funny Comedians (Who Happen To Be Women)” at Punch Line Philly and currently co-hosts “Oh Honey…A True Cringe Podcast” with Jillian Markowitz, outdd this spring. 

In addition to her impeccable timing and solid jokes, Dee offers me, and maybe you in some ways, a route to thinking of us as kindred nerd spirits. Both from Delco, we also both attended Interboro High School and were living on the same street at the same time. We were definitely in the same rooms well before either of us decided to become comedians. It makes the world feel a little smaller in a really cool way. 

The first thing she said to me ahead of our interview set the tone. 

 “All right, I’m gonna say thisand take it with the spirit in which it is intended – you seem like you would’ve been in color guard.”  

Ugh. Nailed it. 

(Apparently, Cassandra played drums in the band at the same time I was in color guard, which is further proof that we were definitely in the same band room, if nothing else at all, but this is coincidental. She’s just that insightful.) 

Watching Cassandra do comedy is like taking a class in humor without accruing massive amounts of student debt – or without hurting others unnecessarily. Support local comedy, and get your tickets to Cassandra Dee’s first full-length album recording on Sunday, April 10 at 8:30 p.m. online or at the Helium Box Office by calling (215) 496-9001.  

When was the first time you did stand-up? 

In college, I did an open mic at the Laff House on South Street.  The host was the Legendary Wid, which I found out later. I gave him my real name and he was like “No one uses their real name!” so he gave me a stage name which I use now. I went up and I did one set, and the first time is supposed to be terrible but it went OK. And then I was just like “I’m never doing this again” and I didn’t do it again for over a decade. 

I’m putting it in print so everyone knows. Not your real name, but the fact that the Legendary Wid gave you your stage name. What did comedy look like after the hiatus for you?  

I did a second open mic in 2012 and a third open mic in 2014. When I did that mic, the manager of Helium invited me back to audition for this thing called the Dirty Dozen. The audition went terribly, but that positive reinforcement of “this is your third time and we noticed you and want to hear more from you” kept me going until things started to actually work out.  

What are some of your biggest comedic influences? 

When I was little, I was introduced to two very distinct types of comedy by each of my parents. My dad was very into George Carlin and Richard Pryor, and I would see my dad watching that and laughing. And then when I was a little older my mom got really into Paula Poundstone, Ellen Degeneres, like, people who would be wearing shoulder pads, sometime in the early ’90s. That’s when I really started to understand jokes, and I really liked when you thought someone was going to say one thing, and they started to say another thing and surprised you. I always liked the concept of jokes. I got really into Margaret Cho and Wanda Sykes.  

But the thing that actually made me start doing comedy was watching Mike Birbiglia’s movie, “Sleepwalk with Me.” When that came out in 2012, I was like “No, maybe I can do this. I haven’t tried this in ten years, maybe the overwhelming urge to throw up when I’m on stage is not so terrible anymore. He seems nervous at first and he gets used to it, maybe I’ll get used to it.” There’s something about that movie that just made me be like “I can do this.” Not “if he can do it, I can do it” but “people can do this, and I am people.” 

We were both born and raised in Delco, which is a very specific experience, even though it’s clearly different for everyone. What was your experience like? 

The best way to encapsulate my experience in Delco is in one short little anecdote that is easily digestible. When I was in high school, I used the word “behoove” in a sentence, and I got made fun of for three months. I never fit in in Delco. My friends and I joke that our school motto was “Football.”  

I was a very sensitive, thoughtful kid who loved learning. I read books because I loved books, and my brother read books to get a free pizza. I grew up feeling like I was never going to fit in anywhere, and as soon as I started doing stand-up comedy, I was like “I’m not as weird as you all made me think I was.” 

Is there anything you would like to tell your fans/future fans before they come out to see your album recording? 

I want people to know that my album opens with an incredibly silly joke, it ends really dark, and there’s a lot in between. I would like to explain that there are jokes about suicide, but I feel like I can’t give content warnings in a helpful way because when half of the people see content warnings, they’re like “fucking Millennials.” The other half is like “you’re making fun of me cause I’m a Millennial.”  

There’s no way to say those words in a way that I feel is actually useful, like “Hey, if it’s going to upset you to hear myself making fun of my own experience of being suicidal, then this isn’t the show for you and that’s OK. I can give you recommendations of very funny people who don’t talk about killing themselves.” 

I’ve always admired how open you are both in your comedy and on social media about mental health and your personal journey.  

For a long time, I kind of felt like comedy was enough for me to deal with mental health problems, so a lot of my jokes ended up focusing on it because it was the only way I was dealing with it. It helped because it enabled me to look at the things I was experiencing from a different perspective. To look at them from the angle at which they’re funny means you’re not looking at them from inside where it’s scary and hard. It did help, but more importantly, it helped me get to the place where I could go to therapy, it helped me get to the place where I could find the right medicine, it helped me get to the place where I could actually deal with it.  

Comedy has a way of making us feel less alone and more connected through jokes and shared experiences. What do you hope your audience takes away from seeing you perform? 

I definitely hope that if people see me telling jokes about depression, suicide, and bullying, they feel less alone. I hope it inspires them to want to get help and feel better, especially now that I’m not actively in it. I still tell jokes about killing myself because it was such a huge part of my life, but for the first time that I can remember, I don’t feel like that anymore. I literally do not remember life before depression. It started when I was 6 or 7 years old. I really hope that people who listen to this album or come out to see it feel less alone if they are depressed. I want them to feel less alone and I want them to feel like there is hope because I’m a fucking mess and I got better. If I can do it, literally anyone can do it. 

  • Aubrie Williams is a writer/comedian who has been performing sketch and improv comedy in Philly and comedy festivals across the U.S. for over a decade. She was a member of King Friday (improv), ManiPedi (sketch), and Goat Rodeo (sketch). Currently, she is one-half of King Friday Productions, a production team she co-created with her best […]

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