A Toast to Claudia and Jackie Oshry

BY: Nikki Chwatt

The dynamic sister duo Claudia and Jackie Oshry have spent the past six years growing their chart-topping millennial podcast, “The Toast.”

Now, they’re bringing their witty banter and up-to-the-minute pop culture discussions to the Hamptons with their live residency, Girly Swirlies Night Out! In this exclusive interview with Spotlight, the sisters share all about this intimate and immersive experience and what they’re looking forward to most about spending their summer Out East.

Like many, we’re big fans of your show “The Toast.” But for those meeting you both for the first time, tell us about the podcast.

Claudia Oshry: We started in 2017 with a daily live show for the millennial audience to talk about pop culture from two hilarious sisters. From there, it evolved into “The Toast,” our daily millennial morning show podcast that covers various topics, including entertainment, news, and our personal lives.

Congratulations on selling out “Girly Swirlies Night Out” in New York City in one hour and breaking the record for the fastest sell-out of three shows in the 25-year history of the Westhampton Beach Performing Arts Center. What can those who were able to get their hands on tickets expect?

Claudia: The show will celebrate “The Toast” with fun games and exciting new segments, similar to what we cover on our Patreon and podcast. It will be pop culture–heavy, but most importantly, it will be focused on fun. We want it to feel like a true girls’ night out. Simply put—a good girlie time.

Jackie Oshry: The goal for the show is for our audience to have a great night. Our listeners are working women and moms, so we want to give them an amazing night. They deserve it.

What does having a live show in the Hamptons mean to you both as born and bred New Yorkers?

Claudia: We are Long Island girlies, so having our live show in the Hamptons feels like a homecoming. The Westhampton Beach Performing Arts Center attracts great people, so we’re excited to bring “The Toast” there. It will be super fun and not serious—nothing we do is that serious! Having the show in New York City at the Beacon Theatre for four nights feels extra special, too, because I live in the city and Jackie used to. We didn’t necessarily plan to have the show in both places, but it feels right.

How will you prepare for live shows in the Hamptons? Are there any favorite local shopping destinations you will be hitting?

Claudia: We have been thinking about our looks. We are both worried about what we’ll wear, so we may be hitting Main Street.

Jackie: Yes, our outfits are important to us. The vibe of New York City and the Hamptons is different, so our looks for city shows will be different than the Hamptons ones. We want to look appropriate for both places.

What are you looking forward to the most about summering Out East?

Claudia: I’m on this wellness journey, so I’m looking forward to eating so much fruit. Fruit in the Hamptons is the best, especially from the little roadside farmstands. I also love Round Swamp Farm and its selections of precut fruit.

Jackie: This July 4th, I’m looking forward to wholesome family time, eating a hot dog, and hopefully having great weather—you know, some good all-American fun.

What advice do you have for creatives looking to get started or advance their careers?

Claudia: Just do it. A lot of people talk about what they want to do, but all the time you’ve spent talking about it, you could’ve just been doing it. Don’t be worried about what others think of you and your ideas—just get started!

Jackie: Remember, how you start will not be how it winds up. You have to start and learn as you go. So put yourself out there and drown out the outside noise. Be unashamed and confident—even if you don’t feel that way. Simply put—fake it till you make it.

What’s next for “The Toast”?

Claudia and Jackie: We’re big fans of blooming where we’re planted, so what’s next for “The Toast”? Hopefully, a lot more of the same!