Meet Olivia Webb | Actress and Producer

We had the good fortune of connecting with Olivia Webb and we’ve shared our conversation below.

Hi Olivia, putting aside the decision to work for yourself, what other decisions were critical to your success?
In the most simplest terms I would say that putting my health, happiness and wellbeing first has been the most important decision. That may sound so obvious and cheesy (potentially) but I do not think that it is said or spoken about enough with actors who aren’t in the famous few. We are doing a job that requires so much of us physically, mentally and emotionally so why should the most important part of our craft (ourselves) not be respected as much as we respect our craft or jobs? I wouldn’t say that this is something that I have perfected yet nor something I have been doing long enough to really give advice on etc, outside of just recommending my friends to do it, but it has changed my work immensely. Whether it be just working out, making sure I get 6-8 hours of sleep, meal prepping, giving myself space to do nothing for a whole day, eating a slice of cake on a bad day or just watching one of the Transformers movies in a dark room alone, I do not view the changes as big or overly time consuming, but for me they work! Because at the end of the day I still have a job to do haha.

Especially as a female in this industry we have an extra added pressure of how we are expected to look and be so taking the control of that into my own hands has given me the extra boost that I believe I needed to fully put myself out there and deal with what is thrown at me- rejection is still so hard though and always will be but it reeeeaaaaally takes the edge off it.

Being physically fit and strong is also very useful within our career anyway so the fact that I am building a joy of exercise, movement and fitness has opened up more roles and opportunities for me.

I am very grateful to the people around me while training and working who pushed me to in this direction and reiterated its importance in harder and busier times.

Can you open up a bit about your work and career? We’re big fans and we’d love for our community to learn more about your work.
I have always wanted to be an actor however there where times where I would detour and say stuff like ‘I’m going to be a lawyer, psychologist or professional athlete’ but at the end of the day it always came back to acting. I started to really take it seriously when I was in year 12 at school (junior year). I applied for The National Youth Theater of Great Britain and got in. When getting into NYT you do a 2 week summer enrollment course and after I had completed that- experiencing a small part of what it would be like to be in acting school- I started to research and look into acting schools I would want to apply to. I ended up applying to the top 5 in London and Scotland and auditioning from October until March. By march I had learned so much but I hadn’t gotten into any of the schools for their full time 3 year courses. I stumbled across The Stella Adler Studio of Acting in NYC on the NYT notice board and saw that there where free auditions taking place in London at RADA so I decided to apply only for more audition experience as I expected not to get in; now I know that going into any audition room with no expectations or pressure can create your best auditions! I got a callback and 3 weeks later I was accepted. It was crazy and I just requested a deferral for a year straight away so I could get everything together and be with my family for one more year while we also grieved the loss of a family member.

In 2020 I moved to NYC and my acting training journey started. It was not easy at all for any of the 3 years however I particularly struggled in my first year and contemplated quitting. I will be the first to admit that in my first year my work ethic was not there in the way it needed to be and I was rapidly falling behind. Thankfully in 2nd year I started to get the hang on dealing with expectations and not crumbling under pressures or viewing a stumble as a failure. This is probably one of my favorite lessons I have learned. With all the performing you do in 3rd year it was just an utter blast!- and it flew by so quickly. There are alway so many challenges to over come and lessons to be learned while you are at acting school however the hardest challenge was adapting to the real world after its all over.

I have always had such a love and connection to Shakespeare, my name deriving from one of his plays- Twelfth Night as well as the my obsession with the Baz Lerman’s Romeo and Juliet when I was younger. I am dyslexic and for some reason the puzzle of Shakespeare intrigued me so much that I preferred reading a Shakespeare play over any book (apart from Harry Potter). This love transferred into acting Shakespeare and being at school only heightened it. After graduation I was looking on Backstage and I was frustrated that the majority of Shakespeare auditions for non-union actors (that would get you good recognition etc) was outside of NY state. I was also very annoyed at the difference between the accessibility of Shakespeare in NY to London. So I thought that I would try my hand at producing and produce a Shakespeare play- that’s focus was to give us non-union actors still the respect, treatment and stability of a union production with a focus on aiding immigrant/foreign actors towards their o1 and OPT visas- something in which I knew I would be going through myself. My dad recommended to me that there was no better place to start than the play I myself was most connected to: Twelfth Night. I had played Viola when I was 16 and was chomping at the bit to give her another go and see how, now being trained, made a difference to how I acted her. We set up auditions, got an INCREDIBLE DIRECTOR (Pete McElligott), found an off-off Broadway space and started the process. Skip to several months later we had a very strong and well loved production that around 500-600 people came to see, a score of 83 on Show-score, almost 500 followers on Instagram and enough money made to pay all the actors, directors and creatives involved. For the first show I have produced, I am pretty damn proud and would hope to call that a success.

I am now in the process of creating a theater company and looking at what is next to produce! While also auditioning and acting being my main profession.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
I am writing all this out as if money is not involved at all! Most of my flights into NYC I get in around 4pm so I am going to have my best friend (Lizzy!) landing around then.

The first thing I would do is take her to a fun happy hour in the city. To mix that with some classic NYC experiences I’d probably take her to a bar just off of Times Square, so when we are done we could walk through Time Square.

For the mornings I would take her to many of my favorite breakfast/brunch spots. Bagels are a must so I would take her to 3! Flatbush Bagels in Flatbush is my favorite so that would be my first, then Liberty Bagels to try out their cool flavors and lastly I’d take her to a classic, Russ and Daughters. My favorite brunch place is The Smith- I tried it for the first time over the weekend and I loved it so I want to go back there ASAP. I also love Clinton Street Baking Company for their pancakes. It’s also a necessity to go to an American Diner so I would take her to Clark’s diner in Brooklyn heights and follow that up with a walk along Brooklyn Bridge.

The views on the Staten Island Ferry is so beautiful and free (which has always baffled me) so that is definitely something I would do with her and then follow that up with a walk to Broad Street for the food there and a drink at the Cauldron- which I have not been to yet but really want to.

If it’s around Christmas time, walking down 5th ave is something I love to do along with seeing the Rockafella tree, Bryant Park market and Pete’s bar all decorated.

I have not been up to the top of the Empire however I really want to and it’s on my list, doing that with her would be so fun along with maybe The Edge.

For dinners I cannot limit it to just a few choices easily however I have always wanted to try The Hawksmore so I would take her there. NYC pizza would be something easy to do too so Prince street and Joes would be a must.

In the most perfect world I would get us tickets to Merrily We Roll Along and a comedy show too, maybe Drunk Shakespeare as well!

Finally I would take her on a walk around Central Park and go get a Levain Cookie to eat on the walk.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
Definitely my family!! This is 100% a very common response I assume but I really wouldn’t be as sane and happy or moving in the right direction without them.

They are the ones who helped me make the move from England to New York (especially my mum who helped me sooo much with working out the visa situation when I was 19 and had no idea how to read legal language) and have been there any time of day when I needed to call just to know how to do a ‘basic adult task’ like unclog a toilet ahah!

I come from a very arts background family while also being on more of the business side of it which has allowed me to have such diverse viewpoint on how the arts world works. It especially helped when I was producing my first play and needed to be able to switch my brain from actor to producer very quickly. My mum and dad both where crucial in the success of that show and I don’t think I could thank them enough for all the advice, time and patience they gave to me during that process. My grandad too! He has been my rock since day one and my best friend, my loudest supporter who had to be given a box of tissues upon entry to any school play I was in from the age of 5.

Instagram: @ojmwebb

Other: Currently our theater company Instagram is @willowtreeproductions so go give that a follow! We will be rebranding soon so keep an eye on my socials for an update!

Image Credits
All the Twelfth Night images are @carannante_nyc