A Belly Full of Laughter with Cindy-Ann Jane

Cindy-Ann Jane Boisson is a Trinidadian-born, Florida-based stand-up comedian and producer, who is focused on making people laugh. And not just any regular laugh but the type of laughter that causes knots in your belly and as Trinis love to say, “makes you want to dead”.

It was clear from a very early age in Cindy-Ann’s life that she had the gift of making others laugh with and at her. Either way, you might wonder how she got into comedy in the first place and has even gone on to be dubbed by some “the funniest woman in Florida”.

It so happened that in 2010, Cindy-Ann moved to Florida where she worked doing temporary assignments as an executive assistant, then in 2014 after sending her son off to College, seriously pursued her career in comedy. She took a stand-up comedy class at The Improv at Hard Rock Fort Lauderdale and performed to a packed audience on graduation night.

It’s not that she didn’t already think she was funny, because truthfully, can you really teach someone to be funny? But rather, Cindy-Ann pursued the class knowing that stand-up comedy was more than just ‘ole talk’ in a rum shop: it involves structure, setup, punchlines and quite frankly a lot of hard work. After gaining a better understanding of how to work and rework comedic material in 2014, she began working the open mic scene for a bit. To Cindy-Ann’s surprise in 2015, the Trinidad and Tobago Diaspora in Florida reached out to her to do a show. In 2016, she was subsequently asked to produce and headline another show. Luckily, she had tremendous help and support in the form of friends forming her tribe called ‘Bess!’ (a group she describes as consisting of “the bess kinda people you need in your life”) and was able to pull off a ‘BESS’ show.

Fast forward to 2019, Cindy-Ann is known for performing at several festivals and venues throughout South Florida and producing five sold out shows. She is currently producing and headlining her sixth show entitled Mauvais Langue—Uncovered. With the coming of this show to Trinidad on April 7th at the Central Bank Auditorium, the XX Team took time to hear a little more from this organically funny gem of whom many can attest has an effortless ability to put a smile on your face. This is what Cindy-Ann ‘CinCin’ Jane Boisson had to share.

XX: Who is Cindy-Ann Jane, anyways?

CJ: Aah…I’m ah Reds from Paramin. I’ve come to realise that who I was does not define who I am nor will it determine who I become. Unfiltered, if you don’t want the truth, please don’t ask my opinion. I love to ‘cuss’, not in a malicious kind of way but I believe swearing was invented to add colour to any language. Prayerful. I know…“a prayerful cussbud?” It happens more often than you know. I don’t love everybody. Am I often overwhelmed with emotions? All.The.Time. I think people confuse emotions with love; not everybody is lovable. Definitely an over thinker! I can and will think any idea to DEATH and bury it too so I guess that makes me methodical? Oh gosh, I’m not easily swayed. You’d pretty much have to walk over a cliff to prove that you’re blind.

Yeah! Mama didn’t raise no fool. Strong-willed. Yep! I’d walk over the same cliff to prove my point! I love to laugh and I truly endorse the tragedy + time = comedy equation. It’s the truth. Everything becomes funny over time. Honestly, I am that little girl who misses her dad a lot. 

What has the experience been like as a Caribbean female comedian living in Florida?

I’ll deal with being a female first. It’s not as it used to be. We’ve had great female comediennes, the likes of whom have made their mark in the comedy scene such as Joan Rivers, Wanda Sykes, Ellen DeGeneres, Kristen Wiig. It’s still very much a boys’ club but there’s now a heavy hitting girls club that boasts of some great comedic talent and one that we ladies can aspire to one day belong to. I’m also lucky to have some very funny female comedy buddies who I enjoy working with.

I noticed you said Caribbean and not black and that in itself has been a part of my experience. It’s an interesting topic and one I’m delving into but in the meantime,  I address it in my set because it’s real. Being a Trini female comedian in Florida has worked for and against me. People loooove my accent. They sit there and become so enthralled by it they forget to laugh then approach me saying: “you are so funnyyyyy.” I’ve had to slow it down and enunciate — it’s like learning to walk all over again. I use a lot of it in my set. It’s funny! I’ve performed in places where people have asked me what I was mixed with ummmm…Trini and Trini!

Oh, and forget about them getting my name right! I use to go by CinCin Boisson. No one — I repeat, no one — ever got my last name correct. I changed it, dropped my last name, now go by my first and middle name, thinking that should do it. Nope! 

What has been your biggest struggle being a woman and a comedian?

Having people take my suggestions/recommendations seriously. As a producer and performer, I have a vision and there have been times I walk into a meeting and immediately I can feel the energy change. Also, open mics. Open mics are a necessary evil. It’s where you get to comb through your material and see what works, you can get some feedback from fellow comics. However open mics are usually very late at night, more than an hour’s drive away, in a dive bar. Open mics spelled backward is “struggle”…look again you’ll see!

Do you think being a woman affects how people receive your jokes at your shows?

It depends on my set and the audience. People see me and think gentle, quiet, reserved. Then I take the mic and spew one swear one after the other and mash up de show! I kid, I kid. I don’t spew my swear words; I enunciate them like the genteel lady that I am! Seriously, I think once they get over the initial shock factor (that I am not the executive administrator for the club), they can appreciate and relate to my jokes.

What keeps you creative and inspires your content for comedy?

Life experiences. I’m very observant and I am obsessed with how much people try to convince themselves that animals are just like people.

What have you accomplished in your career thus far?

Being featured in this magazine. Are you kidding me! I’ve now produced and headlined five sold out shows! What that means is that I create opportunities for myself and others while making real people laugh. I’ve earned the love, trust, respect and support of so many people. I have a family of supporters in Florida without whom I would not have accomplished anything! Nutten! My family at home (in Trini) are always so encouraging, supportive and full of that kinda extra seasoned love! Couldn’t do anything without them either. Nadas. Two years ago, when I produced my first show at home (Trini is home), I never imagined I’d be doing it again — and now again. Earlier this year, I produced and hosted a show for a non-profit organisation that provides people with crisis, health and human services support. All proceeds benefited their cause. Last year, I was invited to perform in Toronto!  I’ve been invited to do the same show again this year.

I’ve got a long way to go, I’m still finding my voice on stage, honing my material, learning to channel that nervous energy because let me tell something to you! It is nerve wrecking! I’m in that self-discovering stage you know?

Everyone has a moment in their life that has them choking and dying with laughter, tell us about a moment like that in your life.

A moment you say? Girl, I laugh all the time! Yep, the choking kinda laughter. I think I’ve actually died a few times, too! If anyone can single out a moment they are not doing this laughter thing right at all. Tell them check me.

What is it like balancing being a mom and a comedian?

There’s nothing to balance. He is a 24-year-old, young man, charting his own course. I done balance long, long, long time. We have a fantastic relationship and if ever he gets a hold of my new number and address he can call or visit anytime.

Tell us a short joke!

Gasparillo Buck. No? Too short?

Sache Alexander

Editor in Chief

Sache loves all things Beauty & Caribbean and she enjoys discovering a combination of both!

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