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Zach Masso

@zachmasso

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Z or Zach 🌟
Chi 🏙️ #Puro956
Actor. Singer. Playwright. Comedian. Amelia Earhart. 🎭
@earhart2hart

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After an 89 year hiatus from the Aviation Industry, Amelia Earhart is making her COMEBACK at the Annoyance Theatre this Fall!

In this two-act dramedy, witness Amelia Earhart fight for redemption in the public’s eye. With a wild cast of characters working against her, will Amelia be able to land the ultimate comeback or will she vanish once more…this time into a fate worse than death…OBSCURITY!

Written by: @zachmasso
Directed by: @amy_allen & @ohhhiris
📸 : @selfoto

Find Amelia Earhart in “Earhart 2 Hart” • 7:30 pm • Thursdays in September • The Annoyance Theatre • Tickets Available at theannoyance.com or via the link in bio! by @zachmasso

And when I’m back in Chicago, I feel it…

(The “it” is “Stunning!”)

📸: the absolutely stunning and fantastic @livemalayastudio once again, they have outdone themselves!! Give Japo a follow, she is the best! by @zachmasso

I guess you can say… I give the heart 🫶 ♥️

📸: @ethan.c_k

(^Make sure to give him a follow I absolutely ADORE his work and had such a blast!!) by @zachmasso

And just like that…she has vanished once more…to a bright BRIGHT future!

Earlier last year, I asked myself, “Why do I want to be successful?” And I came to the honest truth… “I want to make something big. I want to be able to create something wonderful on the grandest scale that I can. I want to show the world I can.” And I realized…maybe I don’t have to wait for the success I’m looking for to do that. And in and of itself, I wanted to write a show that paralleled my journey. And I wanted to write it about a woman who was my inspiration. And thus, Earhart 2 Hart was born.

Last Thursday, we closed my favorite show to date. My biggest passion project. And along the way, I had wonderful WONDERFUL people helping bring it to life.

From the start, @amy_allen and @ohhhiris showed just as much devotion as I did in building and helping this show grow. As directors, they helped shaped this show into something magical.
We had the wonderful @selfoto capture the BEAUTY our show held with her amazing and stellar photography.
We had an absolutely stellar cast who each shined and always had each others’ backs.
Understudies who absolutely ROCKED their show and who always stepped up to the plate.
A kick-a tech/SM in @aj.hernandezsortore who is the absolute BEST.
And most importantly our wonderful audiences who showed up every show, ready to have THE time of their lives!

This is not the end, but just the beginning. Of Zach Masso. Of all my wonderful cast and crew. And of Amelia Earhart….And I mean…Who’s to say she can’t make another comeback? #LetHerFly✈️💕

(PS, you will be seeing MORE Earhart 2 Hart posts to come this week teehee. It was a BIG show!!) by @zachmasso

Is tonight the night where Amelia Earhart vanishes once again? Find out in our Closing Night performance of "Earhart 2 Hart" at 7:30 pm!

📸 cred: @selfoto

Tickets can be found at tinyurl.com/earhart2hart

#chicagocomedy #ameliaearhart #comedy #theatre #annoyancetheatre by @zachmasso

May I just say, a ROUGH year to bet against Zach Masso 🌟✨💕

(Also, I’ve been limited tag wise but also my loves @rothdaddy @twinkjesuslovesyou @t0mcan ) by @zachmasso

What’s to HART about “Earhart 2 Hart”? Well…EVERYTHING!

But seeing is believing! And you can see AND believe that Amelia Earhart is BACK! Thursdays at 7:30 pm at @the_annoyance running through til Oct. 1st! ✈️🗺️❤️

#chicagocomedy #ameliaearhart #theatre #comedy #annoyance by @zachmasso

The most in-demand celebrity on Cameo in 2026: Amelia Earhart!

But you can check her out LIVE in Earhart 2 Hart, Thursdays at 7:30 @ the Annoyance Theatre (running through til Oct. 1st)!

#chicagocomedy #Theatre #AmeliaEarhart #Cameo #POV by @zachmasso

It’s OFFICIAL! “Earhart 2 Hart” is @chicago_reader recommended!! Link to full review in bio (beware of a few spoilers)!

📸: the wonderful @selfoto

What an honor it is to be Reader Recommended!! And to receive all the beautiful and glowing remarks from @kerrymreid ! To see that our work has landed with audiences the way we envisioned means everything to us! And thus, Amelia Earhart’s comeback has officially BEGUN!

Catch our Reader Recommended show, Thursdays at 7:30 pm at the Annoyance Theatre (running through til Oct. 1st!) • Tickets at tinyurl.com/earhart2hart or at the link in bio

#chicagocomedy #ameliaearhart #theatre #annoyancetheater #letherfly by @zachmasso

Amazing showing of Practical Magic last week with our cast @emmanueljrosshartway @marissacomedy @zachmasso

Our audience showed up with magic to spare.

Catch us at our next show: O Brother Where Art Thou? on Sunday to laugh-along to another great movie with Chicago’s funniest comedians! by @zachmasso

The NEWS!! She’s making headlines! Amelia Earhart has officially made her @daytimechicagotv debut!! ☀️

Thank you so much having us on the show, we had an absolute blast! If you would like to see the full interview, check out the link in our bio.

But you know where you can also have a blast? Catching Earhart 2 Hart at The Annoyance Theatre!

Thursdays • 7:30 pm • Sept 10, 17, 24* (U/S show) and Oct 1 • The Annoyance Theatre • Tickets in Bio • or at tinyurl.com/Earhart2Hart

#chicago #chicagocomedy #theatre #ameliaearhart #daytimechicago by @zachmasso