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20 Questions With Stefano May

The rising pop singer-songwriter on playing for the Pope, judging the judges & more.

Stefano May is a man on the move. In more ways than one. The Italian-born, Florida-based popster’s latest single False Horizon is a festival-inspired charmer about finding your inner peace, no matter the pace of your soul. Featuring twangy guitar and an anthemic chorus, the song takes you to a place of refuge from the moments in life that shake us up and leave us guessing. Produced by Chico Benett (Lady Gaga, Madonna, The Killers, Prince) the textured eclectic blend of instrumentation culminates into a perfect blend of romantic Hollywood angst and soulful reckoning for a song about embracing one’s inner journey. Today, May takes a detour into the weeds with my absurd questions. Let’s see how he handles this turn of events.


Introduce yourself: Name, age (feel free to lie), home base and any other details you’d care to share — height / weight / identifying marks / astrology sign / your choice.
Stefano Maiuolo (Stefano May) based in Miami, Florida, where I enjoy gardening, my studio, and our four Pomeranians. 5’8”, 145 lbs., mole on my right cheek, Capricorn rising Scorpio.

What is your musical origin story?
I was born into a musical family. My parents both sing and my father plays multiple instruments. I started performing locally as a young child and by the age of seven was on a nationally televised show, singing Batti Cinque which became an anthem for child labor abuse. My childhood mentor was acclaimed Italian singer/songwriter Franco Fasano and with his and my parents’ encouragement, I later went to the Conservatory of Rome to sharpen my piano skills and ultimately ended up on the Italian talent show Amici.

What’s your latest project?
Releasing a series of singles, filming new videos, writing new music / scores for film and booking live performances again.

What truly sets you apart from other artists?
I think that all artists are amazing and everybody is a unique source of creativity and passion. Having lived in different cultures, the ability to speak four languages and understand different mindsets makes it easier for me to communicate more broadly. The deep study into classical music that I accomplished at the conservatory taught me how to use the past in order to create the future.

How will my life improve by listening to your music?
This is a great question. Based on the fact that I like to write about scenarios we live in daily, I always try to communicate in every song that I write the hardest situations in a very positive way and offer a solution for me and my listeners. I strive to understand different perspectives and offer a way for people to escape their reality through listening to my music.

Tell us about the first song you wrote and / or the first gig you played.
The first song that I wrote was absolutely horrible. I wrote it in Sicily while doing a rehearsal for a live show with my band. It was my first attempt and it wasn’t great but it made me feel like a free man. In that moment, I had many writers writing for me and even with the beauty of their music, I always felt limited in not being able to tell my own stories. That sensation of freedom gave me the power that I needed to keep writing until I found my way to write music. My first gig … wow. I performed a 60-minute show for my neighbors. I built my own stage and used Christmas lights to make the stage more colorful, I used my father’s amplifier, microphone and the B-side of his cassettes that had the instrumental tracks. I consider these shows my first gigs and they were just so much fun and I cherish the memories of them still today.

What is the best / worst / strangest / most memorable performance you have given?
Best: At the 2000 Jubilee at the Vatican, where I performed for Pope John Paul II.
Worst: when I had to sing a song that didn’t reflect myself and it was on an instrumental track where I couldn’t play the piano for TV needs. (very frustrating).
Strangest: When I played at a golf resort in Tuscany and people were eating the entire time (I like creating a connection with my audience and the sounds of silverware and plates didn’t allow for that).
Memorable: On Amici in 2009. A judge on the talent show had been provoking me with slanderous statements and he told me to “surprise him.” I chose Un Giudice (A Judge) because the songwriter had an anarchic wit — the lyrics referenced a judge who was shortsighted enough that his heart was close to his rear end. I felt performing this song was a clear and diplomatic way to express my feelings towards him, the next day Sony Music Italy offered me my first contract.

What is the best / worst / strangest / most memorable performance you’ve seen?
Best: It would be a toss up amongst Celine Dion in Las Vegas, Dolly Parton at the Hollywood Bowl and Emeli Sandé in Milan. I would lean towards Emeli because she is close to my age, her experiences in life are similar to mine and I feel very connected to her stories.
Worst: I was at a show in Miami where an icon cursed and talked about her body parts. We left halfway through the show in disgust.
Strangest: At a Christmas performance in L.A., where a very iconic artist just didn’t measure up singing Christmas songs in comparison to his very famous catalogue.
Memorable: Sir Elton John in Milan as he performed his final tour in Italy in front of 50,000. I have seen him so many times and on this production he went above and beyond. In his farewell tour, it feels like he is supernatural, that he is already in a state to see himself from above while he is singing and playing with such perfection, almost like not belonging or being subject to the rules of this world any longer.

What living or dead artists would you like to collaborate with?
Living: Sir Elton John.
Dead: I would have loved to even play the piano with/for Aretha Franklin.

What artist or style of music do you love that would surprise people?
Classical music, Janis Joplin and Björk.

What words do you hope people use when they describe you?
Real, soulful, passionate, honest, funny, and unique.

What useful (or useless) skills do you have outside of music?
Useful: I love cooking, gardening and other activities using my hands.
Useless: I am overly particular about order, cleanliness, routines, and things of that nature. Some might think of me as a royal pain in the ass. 🙂

Who can you do an impression of?

What do you collect?

If money was no object, where would you live?

What would you like to be reincarnated as?
Nothing, because that means that I did not achieve the mission that was given to me in this life.

Which historical event do you wish you had witnessed?

What’s your idea of perfect happiness / total misery?
Happiness: The serenity of health.
Misery: When a person doesn’t have any way to be creative.

What are your pet peeves?
I must have a clean home environment, and I have a very strict morning routine.

What’s your greatest regret?
Not going to see the last live performance of Aretha Franklin.

What are you afraid of?
I am afraid of the lack of culture that is building in today’s world.

What would the title of your autobiography be?
Stefano: I found My Way.

What’s your motto?
Hope is an excuse for failure, so just do it!!!

What’s always in your refrigerator?

If you could change one thing about yourself, what would it be?
I can’t think of anything structurally, but I am always working on my behavior.

If you had one day to spend as you please without any consequences, what would you do?
I would travel back in time and spend a day with Chopin.

What’s the silliest thing you believed as a child?
I believed that babies were born from a kiss

What was your favourite class in school and why?
Philosophy, because I always loved to know about the evolution of human thinking and my professor was so DOPE.

What’s the best and / or worst advice you were ever given?
Best: No matter what the trend is, always be yourself and be real.
Worst: The same as the best, LOL.

Check out Stefano May’s videos above, sample his music below, and keep up with him at his website, Instagram, Facebook, Twitter and TikTok.


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