Casey the Icon

Graphic Artist and Comedian Casey the Icon Will Be Famous by Age 26

The Twitter timeline is not for the weak-hearted, especially if you’re following the self-proclaimed Kanye West of comedy, Casey the Icon

Casey Ross’s tweets border on the line of problematic and hilarious – poking fun at any and every one, including himself. Contrary to popular belief, the aim has never been to offend his followers. After his own struggles with mental health, Casey recognized the effect that words had on his confidence and will to pursue his passions. Now, he’s hoping to use humor as a way to tackle those insecurities and embrace his shortcomings as a fact of life.

Reflecting on his chosen style of comedy, Casey shares, “When I was the short, bald kid with glasses, I had to learn that words don’t matter. I decided to be the coolest bald person I know. Casey the Icon is an entirely different aura that is confident, outspoken and different. That’s what I want other people to do.” 

casey the icon logo, photo taken by @ronthedon on IG.
Photo Credit: @ronthedon

Casey the Icon isn’t just a comedian for social media. His most recent claims to fame include digital art and creative design for a few of Indianapolis’s up and coming brands. 

He remembers his artistry beginning as early as grammar school, “I was the class clown. I’d draw on my tests instead of actually completing them. I knew at a very early age that I’d make people laugh and do artwork for the rest of my life.” 

While his classmates dreamed of growing up to be basketball players, doctors, “or whatever,” Casey’s plan was to be famous by age 26. He’s 25 now. 

Read as Casey the Icon shares his start in comedy and fashion design and how struggles with mental health inspire his artistic work today.

This interview has been lightly edited for clarity and brevity. 

Casey’s Start in Entertainment

You’re a comedian, you draw, you’re a fashion designer and a graphic artist. That’s a handful. What’s your main focus? 

All of the above! In elementary school, I was the class clown. I’d draw on my tests instead of actually completing them. I knew at a very early age that I’d make people laugh and do artwork for the rest of my life.

Once I graduated from Lawrence Central, I went to the Art Institute of Cincinnati for animation. That’s where I found my confidence and an artistic signature. 

So you wanted to make cartoons? 

I knew I was funny and had a talent for drawing, so I wanted to create my own cartoon show. I had one particular cartoon that I worked on every chance I got. As I went through life on campus, I got distracted and saw myself going down a road that I didn’t want to go down. Comedy became a different path.

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Working like it’s 3 of me

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Comedy became a different path.

I was randomly asked to host an open mic because the MC bailed on the show. I was nervous because I’d never been on a stage. When I got up there, I was just being myself and people loved it. That’s what sparked something in me. Like, damn! I could do this! 

I was already contemplating dropping out of college because I found myself going down a totally different lifestyle path. I was getting into trouble and doing things that weren’t Casey. After the comedy show was when it all hit me. I dropped out the next day. 

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In the Gym

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Some people would take the open mic experience as motivation to continue on with school. What made you choose the opposite route? 

At the time, I thought that I could go back home and make money from comedy. Of course plans don’t go as usual, so I got a job at the Cleaners. [Laughs.]

People already knew me from a group called 2Live – we threw parties back in high school – but I gained more popularity from social media, especially Vine, under the name @itsfunnycasey. I’m just doing this to make my friends laugh, but people that I didn’t know were enjoying them. One moment that changed my life was at a New Year’s Eve party, one of my old friends came up to me and said, “Casey, I don’t think you understand how much you helped me. I’ve been going through such a depression and I go to your videos to make my day better.” That’s when I knew that it wasn’t just about making people laugh, but literally helping people’s lives. I understand how that feels – to be going through a dark period and really needing something to cheer you up. This is what it’s for. 

Eventually, I got so big from @itsfunnycasey that the owner of the cleaners where I was working told me I had to stop doing the videos at work. I thought they should’ve hired me to do some commercials! [Laughs.] I did two more days worth of videos because there were ideas that I had to do at the store, but eventually I just quit working there.

Struggles with Mental Health

The cleaners seemed to be an important setting for your comedy videos. Did leaving impact your engagement in any way? 

The videos didn’t seem to be funny to people unless I was making them at the store. I got really depressed and felt like my purpose was slipping away from me. I started losing my hair because of alopecia induced from stress. I couldn’t find a job and I really wanted something that involved my passion for art and comedy.

I eventually started doing open mics with another comedian from Indianapolis named Dre the Actor. Even if there were only two people in the audience, we were hustling shows. That’s where I found a little more of my identity. 

How did you push yourself to be funny for other people during your depression?

I didn’t have anything else. Art and comedy were the only two things that I wanted to do.

I didn’t have anything else. Art and comedy were the only two things that I wanted to do.

How do you take care of yourself mentally today? 

When I knew that I wasn’t happy, I manifested something different. Whether it be relationships, friendships or jobs, everything that I go through is for a reason or a season. I just try to remember that something greater is coming. 

I was so down yesterday, thinking about how I’m not even halfway to where I want to be in life. But then I thought about it – two years ago, I wasn’t where I am now. I have to be okay with where I am currently, even though I want to do more, because everything happens in its time. 

Casey the Icon

I have to be okay with where I am currently, even though I want to do more, because everything happens in its time. 

Bridging the Gap Between Graphic Art and Fashion Design

Up until now, it seems like your focus was mostly on comedy. When did you start to incorporate graphic art?

The graphic art just started about two months ago. I downloaded Adobe Illustrator and Photoshop on my phone so that I could work on the train. I’m doing this all with my finger, not with a stylus or anything like that. Three days after downloading the apps, Kim Kardashian retweeted one of my drawings. 

That’s crazy! When did your talent for drawing translate into fashion design? 

In high school I always drew cartoons. If you wanted a cartoon drawing, you went to Casey. People really liked the clothes that the cartoons were wearing, so I started making t-shirts for me and my homies to wear. Once I got older, I learned more about fashion and connected with Grant to be a creative designer for 7House. Grant connected me with Keenan from Silent Hustle, and I’m now also the designer there. 

When I found out I would be Creative Designer for the brand, I started to learn from people like Virgil Abloh and Matthew Williams. I’ve learned how they set themselves apart by branding their ideas strategically and shifting perspectives. They think differently.

It’s so interesting that you say that – it seems like the theme of your life story has been to think differently. Most people would’ve finished school and pursued these passions in more of a straight path.

I’ve seen myself going down the road that was built for everybody and then I see a different way. 

I’ve seen myself going down the road that was built for everybody and then I see a different way. 

All Signs Lead to Chicago

Why leave Indianapolis? It’s where you got your start! 

After becoming Creative Director for 7House and Silent Hustle, I was still depressed. I was still doing open mics and comedy shows, but I felt like I wasn’t doing enough. I vented to one of my homies and he told me to simply ask for a sign. I kid you not – he told me a story of being on a boat and he said, “God, give me a sign. If I should do this, my hat will blow into the water.” At that exact moment, the boat hit a wave and his hat fell in the water. That story always stuck in my head. 

Fast forward a few months, and my life had totally spiraled. I got kicked out of my cousin’s house and someone stole the license plate of the car that I was living in. I’m driving around trying to find a new place to live and it starts raining. As I’m rolling my windows up, the driver in front of me hits the brakes. I hit them and totaled my car. My entire life was felt totaled. 

I felt totally defeated. I moved into my friend’s house started working at Rally’s. I figured I should just work a regular ass job, do comedy shows and artwork when I could, and start over. 

You didn’t have a choice! 

Right! I couldn’t afford to keep following my dreams like I was before.

One day at Rally’s, every one called off, including the manager. It’s extremely busy and the only workers are myself, a fill-in manager and a 16-year-old girl who had never worked there before. I had already been contemplating moving away and starting over completely, so I’m thinking of the story that my friend had told me months earlier. As the stress built up, I said, “If my crush likes my picture on Instagram, I’ll quit my job right now and move to Atlanta.” I’m going throughout the day and the next time I looked at my phone, the first notification was that the girl liked my picture. 

That was on a Sunday. I moved to Chicago on Thursday. 

[Quick shoutout to Bria Bush – the girl who liked Casey’s picture. If you hadn’t been on his IG, he might still be working at Rally’s!] 

Meet the Icon

Did your mental health take a turn for the better after the move? 

A lot of people think that moving to different cities is all glitz and glamour, but that was the worst time for me. In a weird way, this was the best feeling I could’ve experienced because I knew I needed to work on my art and comedy. I stayed in my dad’s basement in Gary and I didn’t have any friends.  That’s when my comedy switched from making people laugh to talking about something of substance. 

My hair started to grow back once I moved to Gary. I was thinking, “Everybody made jokes about me when I was bald and depressed and wanted to kill myself, so I can talk about everybody else.” If you’re fat, so what? You have to embrace it like I had to embrace my baldness. 

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The Family

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So this is where we meet the Kanye West of Comedy. 

Yeah! Nowadays everybody is so sensitive. You can’t talk about one person without being cancelled. When I get on stage, I tell people that nobody in this world is perfect. Even if it’s harsh or mean, it’s funny to somebody else. I roast myself before I talk about everybody else to let them know that it’s okay to laugh. 

Do you think that takes away from the initial intent? What about the girl at the party that said you made her feel so good? And now you’re making people feel a little bad. 

No, I think it helps. I know that I’m coming at it with a totally different angle, but I’m asking people to embrace the things that I’m making fun of. 

When I was the short, bald kid with glasses, I had to learn that words don’t matter. I decided to be the coolest bald person I know. Casey the Icon is an entirely different aura that is confident, outspoken and different. That’s what I want other people to do.

When do we meet the Icon? 

When he’s needed. Comedy shows, social events – but not all social events. Sometimes I’m just Casey and Casey likes to sit back.

Casey the Icon is the one who got retweeted by Kim Kardashian?

Yeah. That was Casey the Icon. Casey the Icon is always in my art because my art is my humor and creativity. I’m putting it all on the paper. 

You don’t seem phased about this Kim K. thing… 

It’s why I know that there’s something greater for me coming. As a child, when we went around the classroom and talked about what we wanted to be when we grew up – most people would say a doctor, a basketball player, whatever. I said I’d be famous by the time I’m 26. 

Famous doing what? 

Any of my talents. One of them has to bloom soon. I just want to be famous so I can inspire everybody else.

So, are you happy that you’re here? 

Yes, I love the fact that I quit Rally’s! [Laughs.] None of this – you and I having this conversation, the interview at ComplexCon, doing comedy shows with Leon Rodgers and Damon Williams – would happen if I stayed at that Rally’s. 

I just want to be famous so I can inspire everybody else.

The Three Words

Describe the Icon in 3 words.

Hilarious, creative and confident. 

Icon is the creative genius, he’s the funniest and most confident person you’ll meet. You can say whatever you want about me, but it won’t affect me because I’m Casey the Icon. And once you see the confidence, it’ll make you confident in yourself.

Follow Casey the Icon on Twitter and Instagram to stay up to date on his creative endeavors. 

Feature images were taken by @ronthedon.

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