Anna Roisman [Interview]

Hello Folks! And welcome back to another fine Wednesday here at Trainwreck’d Society. Just as a disclaimer, I wanted all you fine readers to know that today marks the day that we return to being an American based blog. That’s right. After Just over 8 1/2 years, TWS has relocated back to the states. Posts from our final location will commence on Friday, but it is suffice to say that it will not be the Embassy Suites out side of the Seattle-Tacoma International Airport. Although, I do recommend their breakfast sandwiches. Very good.

Any way, the real reason we are here is showcase some words from the insanely hilarious and immensely hilarious comedian of the day, it’s Anna Roisman, Everyone! Anna is a beloved comedian and writer in the world of comedy. Her work has appeared on everything from MTV, College Humor, and People Magazine. I will be the first to admit that I first became aware of Anna’s brilliance on a platform that, which is technically supposed to be used, actually sort of made me sad. Yes Folks, it was that damn again. But, when so many of the people from the world of comedy follow somebody, and their presence is just so damn hilarious, it’s too easy to become a fan of somebody so damn talented.

So Folks, I am going to take my jet-lagged ass back on to bed, but I felt it absolutely necessary to get these fine words from one of the best voices in comedy today. We are so excited to have Anna Roisman grace our digital pages today. She’s a multi-faceted human being, but a one of a kind hilarious. You’re going to love what she has to say. So enjoy some words from the great Anna Roisman!




What initially inspired you to get into the world of comedy? Was it something you wanted to do since your youth? Or did you happen to find yourself in this world one day?

I initially wanted to be an actor and fashion designer “on the side.” HA! I said I’d be in movies and TV and design clothes since I was very young. So I kind of always had the acting bug. Sunday nights in my house growing up were my show nights where I’d put on a show and have my younger siblings be my backup dancers. They were anything from Spice Girls lip sync shows to horror movies. As I got older and started doing theater, I was always cast as the comic relief parts. Never the ingenue, which pissed me off. I enjoyed making people laugh, but still! I’m a leading lady! At the time I didn’t think of “comedy” as a career. I wanted to be on sitcoms though. I started making funny sketches in college and shooting stuff because I was a TV Production major. I was writing spec scripts and I knew it was something I was into. But I moved to NYC to try and audition for theater and film after college. It was then that I found myself in comedy. I felt like an outcast in the musical theater audition rooms. I was like, what am I doing here? I felt much more comfortable doing comedy and realized I could do that and then head back to broadway someday. The dream doesn’t die! The path just changes!

What was your very first paid gig in the world of comedy? And were there any sort of lessons learned from this experience that still affect your work today?

My first paid gig in the world of comedy…that wasn’t a drink ticket… hard to remember! I actually got a job making a music video for a comedy youtube channel a long time ago and they gave me an awesome budget. I had produced and written a few sketch videos of my own with a comedy partner, so having a company trust me with a budget to make them something that I pitched was very exciting!! I had a friend help me who worked at the time for College Humor because I knew he had contacts and we put together an awesome shoot. It was 3 locations, a full shoot day, I wrote it and starred in it, and it felt like a dream?! And I even walked away with a paycheck. I learned quickly that those experiences don’t happen all the time!! I thought, oh I’ll just continue producing these videos and then I will be able to quit my restaurant job! Nope, that was naive. I learned a lot about what it takes to produce a music video and I’ve made some since, so it was a really cool experience.
I always love to find out what are some of the more obscure cities, venues, etc. that comedians have gone up in that may surprise people to know that it is actually a wonderful place for comedy? Especially after the last year, I feel like it may have gotten a bit more strange. So, do you have any places that have intrigued you, before or during the end times?
I thought standup was like, over forever, after the first month or so of the pandemic. The Zoom shows weren’t the same vibe. Then I did a standup show at a drive-in diner place in Astoria and it was the most fun I’d had in ages. Maybe that was because I hadn’t left my apartment? But it was a really fun time and cars would flash their lights everytime they liked a joke of mine, and it felt amazing to be up on a stage of some sort. It kind of opened my eyes to *new spaces* if that makes sense. Also, I used to do my show The Unemployed Show from my couch in the ‘before times’ like 3 years ago, and this couch has been an amazing stage for me then, and now! So yes, my couch.
Beyond the fact that it is pretty much essential for a comedian to have a podcast these days, I am very curious as to what inspired you to create the extremely original, and absolutely hilarious podcast, Unemployed with Anna Roisman? And for our readers who may be unaware, can you tell them a bit about the show?
Sure! We just dropped our 50th episode, which is hard to believe! So back in 2016 I lost my very cushy day job of 4 years at a Venture Capital firm and they gave me a severance package which I had never heard of before. So I was still being paid, and had all this free time. Life was glorious! (Sort of.) So I started a fully produced live stream show from my apartment called “The Unemployed Show.” It was mostly Thursdays at 3pm and we wore pajamas and drank alcohol and I interviewed other unemployed creative people. We played games, we did segments, it was amazing and it became a huge part of my life. After doing 50 live episodes (you can see them all on Facebook!!) I decided to end the live show because, surprise, I got a job hosting HQ Words, the new show on HQ Trivia and I was working 7 nights a week. I knew I didn’t want to give up on the brand of Unemployed because it was something I created and loved. But I was working too much to produce it. So I decided to launch it as a podcast, a few months later. It’s more tamed, we’re not drunk in pajamas, but it’s a space for me to get to know people through the jobs they have worked over the years. It’s fun to hear about people’s stories of getting fired, quitting, crazy co-workers and bosses, and anything else they want to share! Sometimes we have strangers call into the podcast who are unemployed and we give them a pep talk. It’s so much fun and it’s so interesting to hear about people’s journeys and how they handle times of unemployment. You don’t have to be unemployed to be on or listen to it! But if you are? Welcome to the club, we got you.
I would also love our readers to know more about Anna Dyed, a wonderful clothing line you have put out. Can you tell them a bit about how this line came to be, and how they can get their hands on some of it?
Hahaha wow I didn’t think this would make it into the questions! Love it. At the beginning of the pandemic I really wanted to buy all of the tie dye sweat suits I was being targeted on Instagram. The issue was I had no job then and they were all like $300. So, I was like, maybe I can just do this myself. I am very crafty and I draw and stuff. I knew I could do it. So I tested out a few different sweatshirts for material, and found the one I like, and I made myself some stuff! Then I made my mom a sweatsuit, and my sister, and before I knew it people were asking if I was doing this for other people. So I thought it has to be called Anna Dyed because that’s just funny to me, and I made a little instagram @AnnaDyed and I take orders through DM. I can only do so many at once because I live in a small apartment in Brooklyn. So I do them as a “drop” and fill the orders. It’s been too cold to dye now and I duno how much longer I’ll love the trend, but maybe I’ll do some fun pieces this spring?! We shall see…
What else does the future hold for you? Anything you would like to plug to our readers?
The future is something I try not to think to hard about. If there’s anything I’ve learned from this year, it’s that anything can be swept up from under you. So I try to make sure I have multiple projects going at once, and I pray that some of them will sell and get made!!! I’d love to plug a few things – please check out the podcast!!! “Unemployed with Anna Roisman” wherever you get podcasts! Subscribe to it, and I promise you’ll find something you love about it. Also you can watch me hosting HQ Trivia or HQ Words on Wednesday nights at 9pm ET where you can win money. Lastly, my boyfriend Jared and I have produced a bunch of shot-for-shot movie parodies in the pandemic that we’re really proud of. We did The Notebook in our bathtub. It was insane and almost broke us up! The latest one is the movie Seven, but we called ours Eight. So definitely check them out, alongside my soup recipes all on my Instagram: @AnnaRoisman.
What was the last thing that made you smile?
The last thing that made me smile was this sour cream & onion dip I made to go with a bag of kettle chips. Remember sour cream and onion dip? I’m talkin’ the shitty like powder kind. It’s glorious and it made me smile, and that’s important to remember nowadays!!!

About rontrembathiii
write. write. write.

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