Home Read Features 20 Questions With Alessandro Montelli

20 Questions With Alessandro Montelli

The Toronto singer-songwriter on pasta, stage-diving & his love for Linkin Park.

Singer-songwriter Alessandro Montelli took us for a ride last fall, delivering a message of equality, justice and humanity with 1 Race, a  collaboration with Toronto rapper Karizma. You can read more about that HERE. Today, Montelli saddles up and takes a spin through my obstacle course of goofy questions. Will he still be riding high by the end? Read on and find out:



Introduce yourself: Name, age (feel free to lie), home base, other details you’d like to share (height, weight, identifying marks, astrology sign, your choice).
Hey! I am Alessandro Montelli, 29 years old, Italian-Canadian singer songwriter. I was born and raised in Italy but I decided to move to Toronto when I turned 25. I am a Leo, and I gotta say I’ve been very passionate and determined in terms of pursuing a career in music.

What is your musical origin story?
My journey with music starts at a very young age, when my parents influenced me to begin taking piano lessons at the age of 10.

What do we need to know about your latest project?
My latest project it’s a song we wrote while stuck in quarantine, that is meant to inspire people to always do better, to unite and respect each other.

What truly sets you apart from other artists?
I think one of the things that sets me apart from other artists is my use of multi languages when I sing. Growing up in Italy and having studied languages, I’ve always written and sung in Italian, English and Spanish.

What will I learn or how will my life improve by listening to your music?
Well my goal is to make people feel inspired to follow their dreams, and to feel able to take risks. But I also hope people feel understood when they hear my lyrics.

Tell us about the first song you wrote and / or the first gig you played and what you got paid.
The very first song I wrote was actually in English, and it was called Don’t Go Away. Was definitely about my first love. I was probably 17, and I remember I just wanted to get this girl to come back to me, and have a successful relationship. It didn’t go that way, and there were a lot of ups and downs. Can you relate? 😉

What is the best / worst / strangest / most memorable performance you have given?
One of the best performances I ever gave was at Yonge & Dundas square in Toronto, during Youth Day Global. The stage over there is always massive, and the crowd was pretty great! I remember me introducing my new song Life and a group of folks going crazy on the beat. It gave me so much more energy and hype.

What is the best / worst / strangest / most memorable performance you’ve seen another artist give?
Well I have to be honest on this, I do love when artists do stage diving, especially in an alternative rock concert. I remember seeing a couple of bands doing it at my first and last Vans Warped Tour that I attended in 2018, and it was so exciting.

What do you want to be doing in 10 years?
Exactly what I’ve been doing for the past 10 years, and what I am doing now, but amplified times 20. I want to be able to sustain myself and the people I love with my talent and my music, and also help others to come out of stuff like depression and anxiety, which is something I’ve known too and inspire them to believe in themselves.

What living or dead artists would you collaborate with if you could?
I grew up listening to Linkin Park. That is a band that really helped me cope with all those “bad” feelings growing up. And I know Chester (the frontman) was like me, and gave all his heart and passion to his supporters. It would be a dream come true if one day I could link up with Mike Shinoda and the rest of the band to create a song together. Other than this, it would be extraordinary collaborating with Eminem. He’s still the best rapper of all times in my perspective.

What artist or style of music do you love that would surprise people?
I love music and I don’t necessarily judge by genre. I really enjoy listening to anything from Harry Styles to Machine Gun Kelly these days.

What are your favourite songs / albums / artists right now?
I really love some of the latest MGK tracks.

How about some other favourites: Authors, movies, painters, you name it.
J.K. Rowling will always be my favourite author. I grew up with Harry Potter.

Who would you be starstruck to meet?
Julia Michaels. I love her style, music and beauty.

What’s your favourite joke?
Italian ones, but it would be too hard to try to match the meanings Lol

What do you drive and why?
Right now I don’t drive anything specific, but I used to own a Vespa back home and it was great. Riding a “motorcycle” is one of the best feelings ever.

What superpower do you want and how would you use it?
It would be either the ability to fly, or the invisibility.

What skills — useful or useless — do you have outside of music?
Skill wise, I became really good at networking with people. I’m a good listener, and friend.

What do you collect?
This is a weird one. I used to collect clothing tags for some reason. Just loved brands

If I had a potluck, what would you bring?
Pasta!!!! is that a question? ahaah

What current trend or popular thing do you not understand at all?
Some trends, especially the ones on TikTok nowadays, are the most weird.

Tell us about your current and/or former pets.
I had many pets. Fish, turtle, hamster, but mostly a dog. His name was Remington, and it was the cutest and harmless cocker spaniel. But unfortunately I lost him when I moved to Canada, he got sick right after and he has been in my family for 13 years … I know, that’s a long time!

If you could have any other job besides music, what would it be and why?
I had different jobs besides music — retail and food related jobs that I would do in order to produce my music. My dad owns a bicycle store in Bari, and I would love one day to help him a little more with the business.

What’s the best advice and/or worst advice you were ever given?
Best advice I got would be to always be yourself and do what you’re good at. That’s key to succeeding in life.

Watch 1 Race above, hear more from Alessandro Montelli below, and connect with him on his website, Facebook and Instagram.