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First Cigar with Orlando Mendez: The Cuban Cowboy

Cuban Cowboy

So it’s not every day that we have a country singer from Miami. A Cuban cowboy at that. So how did country music become your thing? You were a theater major in college, so when did country music come into play?

I remember finding country music around middle school age, in those teenage years. I had a girlfriend at that time who liked country music and she kind of introduced me to that world. Specifically, it was really Darius Rucker who got me into it because I grew up listening to my dad’s music, Only Wanna Be With You every time the [Miami] Dolphins would lose. “I’m such a baby cuz the Dolphins make me cry,” we’d sing it as a family. And so, I remember making that connection later one day listening to a Darius Rucker song like, ‘I’ve heard this voice before.’ And I remember the exact song. It’s called Comeback Song by Darius Rucker, and I was like, ‘Man, I dig this song. But I think I know this voice and I know this guy.’ I did a little Google search and made the connection. ‘That’s Hootie from Hootie and the Blowfish.’ And then I started going through his catalog and it was kind of like just a gateway from there. From Darius Rucker, I found Dierks Bentley, Blake Shelton, all those guys who influenced me. I loved the stories in their lyrics, I loved the melodies that they were using. There’s something about country. Country music just kind of lit a fire in me, and it was all I listened to throughout my high school years. Life’s got a funny way of working out you know, now I’m singing country music for living.

So, you fall in love with country through the gateway of Darius Rucker, which is pretty funny. Now take us through how you got to this point. Did you just start playing country songs, trying to cover the songs you liked, and then eventually started writing your own?

Yeah, that’s kind of how it happened. As you mentioned before, I was a theater major in college, and I was acting for a while. Pre-COVID I was going back and forth from New York to Miami auditioning for plays, doing the acting thing, it was great. Then COVID hit and obviously it shut down that whole industry and suddenly I had a lot of time on my hands. I thought, ‘man, it’s time for me to pick up the guitar, I love country music, I love listening to it, I love singing it but it’s time for me learn how to play.’ I started playing guitar, started learning all these classic country cover songs that I love. And I’ve always had a passion for poetry, and a passion for stories. So, it was time for me to try to write my own country music. I started mimicking those sounds, mimicking the chords and the melodies. I found my footing in the world of country music and just telling stories about my life and those around me.

That’s insane. Most people learned how to bake or how to butcher a new language. You started a country music career and after starting a local country music band in Miami, we first came to know of you through the talent show The Voice on NBC. How did that come about?

The Voice thing was funny man, it was 2022. We were playing all these shows and I had seen open calls for The Voice a couple of times, just through casting networks I still had from my acting days. I never thought anything of it, I didn’t really want to do that, and a friend of mine one day says, “Hey, I saw this email to audition for The Voice and I think you should do it.” I was like, ‘Man, I don’t want to. That’s not me. I don’t want to do reality TV. I’m not interested.’ And he says, “Well, I think you’re crazy not to do it and if you don’t sign up, I’m going to sign you up.” So I did the virtual audition and like four or five online rounds later, they flew me out to LA for the big Blind Audition.

What was the first song you sang on the Blind Audition and what was going through your mind?

The first song was Beer Never Broke My Heart by Luke Combs. That’s the first song I sang on there, you can still find it on YouTube. I say it to this day, that was the most surreal moment of my life. Right? We had spent three or four weeks in LA in preparation for the audition, rehearsing, interviewing, doing all these things for TV. I was around 99 other people who were given this chance to Blind Audition, some incredible talents so I was just like, ‘man I want one chair to turn. I just want to go on this stage and not be completely disappointed, I just want one chair to turn. Please give me one chair.’

To get four chairs to turn around was the most surreal moment in my life. I never planned on that and never thought about it. It was a huge blessing.

After The Voice you ended up leaving Miami and moving to Nashville. You’re now an independent artist, so you’re not signed to a label, how does that work? If there’s a cigar smoker out there who wants to follow in the Orlando Mendez footsteps, what does that look like?

It’s tough, but it has gotten easier with the world of social media and independent distributors. Right now, I go through DistroKid. So pretty much you can just start a profile on there and put your music right to Spotify, Apple Music and all of that. Not having a label is challenging because you’re competing against all the other independent artists like you but you’re also competing against all the label artists for the same audience. It takes resources, it takes money, it takes dedication, but it’s possible, we’ve been making it happen for a year now and this year is looking great. I have had the big
blessing of being invested in by certain people to allow me to record music and release music. My parents have been pivotal. A man by the name of Wade McGuinn out from South Carolina has been pivotal in helping me fund some of this stuff. And for that I’m grateful and looking for the next next partners as well.

Your latest track, Motherland, is one that you’re pretty excited about, can you play us a bit of it? (singing)

Yeah, I’m sitting here drinking at the southernmost tip, down in the Florida Keys. About to take my last rum-filled sip when suddenly it came to me, I looked out across the ocean to see if I could see, the island where I came from, that still part of me. And sure, I ain’t ever been there, I ain’t ever touched that sand, but it’s where my family came from, and it makes me who I am. This deep-rooted connection that at times I don’t understand, but as I’m sitting here right now, I’ll tell you man. There’s only 90 miles and a cigar in my hand, between me and the motherland.

That’s awesome. And that great line that says, “And a cigar in my hand,” feels like the perfect segue into your love of cigars. Do you remember the first cigar you smoked?

I remember, it was a Romeo y Julieta. I was probably under cigar smoking age if we’re going to be honest, but I remember one of my birthdays my godfather bought me a Romeo y Julieta. He wanted that to be my first cigar smoking experience and he wanted it to be with him and so I smoked one with him. But probably the most special cigar experience is watching my grandfather roll cigars as a kid; he would roll his own cigars. They were tobacco farmers back in Cuba, he didn’t do that here for a living, but he still had a passion for rolling and I remember from a young age watching him roll cigars.

So, what’s your go-to cigar right now?

This Liga that I’m smoking is pretty good but I’ve been smoking Plasencias quite a bit. My go to celebration cigar, though, which my grandfather was a big fan of, is Padrón. So, my go to celebration cigar is that Padrón 1926.

What kind of celebratory moment do you have in your sights for this year that would warrant a Padrón 1926?

There’s a few in my sights for this year. I think one of them would be releasing a song that gets over a million streams. I think that’s coming this year, I really do believe that’s coming, we’re getting there. Another would be when I play the [Grand Ole] Opry, I hope that happens soon as well. I’m also planning an album release this year, so after I release my album, I’ll definitely have a little 1926.

(Photo by Nathan Chapman)


This interview appeared in the Mar/Apr 2024 issue and in the Cigar Snob Podcast #158. Watch it here!


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Categories: Personalities

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