“We purposely waited to do a headlining tour until I felt we were ready to do a headlining tour so that fans could come and go, ‘I know him.’ and let the fans sit with the music long enough and say, ‘I want to come out to a show.’”

As I sat on a couch in a dressing room at Joe’s Bar on Weed Street interviewing Michael Ray, I couldn’t help but think to myself not only how incredibly humble and genuine of a human being he is, but also how smart of an artist he is. While the almost 29-year-old country singer was explaining to me what it’s been like selling out almost every night of his first headlining solo tour, it was impossible not to hear the disbelief, gratitude and excitement in Ray’s voice as he spoke.

“What’s been real cool is just seeing the fans’ reactions and hearing fans sing lyrics to album cuts back and songs that were never on the radio, and seeing people really connect with the album, which as an artist is the most flattering thing.”

I was able to witness the flattery Ray was referring to firsthand that night, as I watched his set from a different angle than I normally would. From the side of the stage (as opposed to the middle of the floor), I watched the crowd respond whole heartedly, as they sang every word back to him while Ray gave 100% to them with his captivating performance. The charismatic singer kept the momentum going and didn’t miss a beat as he played through practically his entire 2015 self-titled debut album. Ray also took time to pay tribute to some of his biggest musical influences and show his appreciation to the artists who he’s been fortunate enough to tour with over the last few years. During the short acoustic set, he partially covered Keith Whitley’s “Don’t Close Your Eyes,” David Lee Murphy’s “Dust on the Bottle,” Sam Hunt’s “House Party,” Kip Moore’s “Beer Money,” and Darius Rucker’s version of “Wagon Wheel.” Needless to say, fans left happy.

It was clear that waiting to do his own headlining tour paid off for Michael Ray in the end, as he put on one of the most energetic and interactive shows I’ve seen at Joe’s Bar, and this is coming from someone who has seen a TON of shows there. He knew exactly how to work the stage, interacting with fans as he went from one end to the other throughout the night. Ray also kept his talking to a minimum so as not to lose the crowd’s interest, only stopping to express his gratitude to everyone for allowing him to do what he loves and get to where he is now. He thanked everyone from fans to the folks at country radio who play his music and everyone in between for making it even possible to sell out his first headlining show at a place as legendary as Joe’s Bar.

During our interview, Ray expressed his appreciation for having the opportunity to open for Darius Rucker last summer, and didn’t hold back when it came to explaining everything he learned and took away from the veteran singer while on tour together.

“His passion for what he does and how he runs everything, not only on stage but backstage…. how he treated fans, how he treated his band and anybody working for him…the people loading in that were just there in the city…I learned a lot about my set, too and learned a lot about covers. He does a lot of different covers that are really cool that I would never have thought about doing. And just how he has this very cool way of being easy and cool, but still getting everything done. He made me feel like it was my tour, made Dan & Shay feel like it was their tour, and just made all of us feel like it was our tour, and so I learned how to treat my openers. That’s the main thing. I learned to make sure that (opening act) Levi (Hummon) knows this is his tour too, and that these are people he needs to win over.”

If you were to see Michael Ray in passing and didn’t know who he was, you might not guess he’s a successful country singer. While the Florida native definitely has more of a “rocker” appearance, there’s no denying the country that comes out when he starts to talk to you. From his undeniable accent and his incredibly polite and hospitable demeanor to the manner in which he speaks, Michael Ray is country to the core. In fact, he comes from a family whose country roots go back generations to a small town outside of Orlando. It’s no wonder the rising country star is so strongly influenced by, and to this day still loves traditional country music; he grew up around it and even played in his grandfather’s band.

“I think I listen to lyrics stronger than I listen to some melodies…growing up and being a fan of and hearing those songs, they were very lyrically driven in those days. So, I feel like I listen to songs just a little bit differently because of growing up in that,” Ray explained to me.

While growing up where and how he did certainly shape who he is as an artist, Michael Ray’s list of musical influences doesn’t stop at just country artists. The charming singer made his love for other genres (such as pop punk, 90’s alternative, and hip hop) known to me during our interview, but explained that he just tends to gravitate more toward the traditional country he grew up around. So although he has a well-balanced musical intake, there’s no denying the country boy that comes out when Ray opens his mouth to sing. Listening to him is literally like hearing the perfect combination of vintage and modern country, totally reminiscent of the 90’s country we grew up on mixed with today’s country sound that surrounds us now. It’s truly impressive how well Ray has taken two different styles of country music and effortlessly created a blend so flawless and smooth that it genuinely pays tribute to the best in both generations of country in the most flattering way possible.

Michael Ray’s self-titled album, that was released just two years ago, is nothing if not the best possible representation of himself, as well as an excellent introduction to who he is as an artist. The album, like Ray, is country through and through with just the right amount of edge to fit seamlessly into today’s realm of mainstream country while still managing to hold onto that wholesome feeling that is at the core of country music. Although Ray only co-wrote one song (“Run Away with You”) off the album, he was careful about choosing the right songs to include.

“I wanted to make sure there were some songs on there where people could get to know me, like “Somewhere South.” Ya know, at the time I lost my grandfather, and it was a tough time but that song is kind of what I felt when I was driving back to Florida. Sometimes you just need to go home for a little bit and just be around some family friends or some family, and just kind of recharge that part of your life. And I wanted to make sure we put the best possible songs on the album, whether I wrote them or not, and just really have a good introduction as a body of music of me to the fans,” Ray explained to me during our interview.

Ray’s first single, “Kiss You in the Morning,” which was written by Justin Wilson and Michael White, reached number one on the US Country Airplay charts, and his latest, “Think a Little Less” (which features Thomas Rhett as a co-writer) is currently sitting at number three and will hopefully be reaching that number one spot soon with all of the radio play it’s getting. In a genre that has an endless number of ridiculously talented songwriters, it would be only natural for artists to feel a certain kind of pressure in order to write the best songs possible to record for their own albums. Michael Ray has his own unique and special perspective, though, when it comes to songwriting, and it’s a direct reflection of just the kind of person he really is.

“To this day if someone gave me the choice, you can write your first hit and it’s gonna be a number one, I still would not write it just because of being able to be honest and being able to celebrate them because the writers, they go through and they write and they turn it in and they hear somebody cuts it, but they’re so focused on writing and writing and getting as many songs cut as they can that sometimes they get overlooked, and they don’t get the credit, they don’t get the attention that they deserve, the celebration of their art. So being up on stage for that number one party and seeing their (Justin Wilson & Michael White) families, and being able to be a part of that was a feeling that was almost just as good as or better than having the number one itself…so it was an awesome feeling…I feel like as an artist your job is to make the best album possible, whether somebody else writes it or not. I love music, I don’t care whether the singer wrote it or whatever, as long as I can relate to it and I can sell it, and that person in the audience…maybe it changes their life. Maybe it helps them get through something…whatever it is I want that song to touch those people, and whether I wrote it or not, that’s all I care about.”

While fans anxiously await new music from Michael Ray with no anticipated release as of yet since the singer is currently working on a second album as we speak, they will be able to see him perform at this year’s 3rd annual Windy City Lake Shake festival on Saturday, June 24th. Being an avid lover of Chicago, Ray said that he’s “super pumped” to play the country fest when I mentioned it during our interview, and added that, “Being a part of this festival this year is gonna be unbelievable.”

The singer has made his love for the Windy City and our new World Series Champs well-known by now if you follow him on social media, and even flies the W flag proudly both on his tour bus and on stage during his performances.

“I love the city, the people, the food and of course the Cubs,” Michael expressed. “Carla and I try to get up here any chance we get just because we love it so much.”

Michael Ray is without doubt one of the most sincere people anyone would be lucky to meet. His laid-back attitude makes him not only approachable, but also very easy and fun to talk to. His appreciation and modesty only add to his already likeable character and definitely resonates with his fans.

“It’s a cool feeling to have people come up to you and say, ‘Hey man, I love your music.’ It’s just a gratifying thing to have people wanna take some time out of their day to say thanks for your music.”

With undeniable talent and a sound that manages to appeal to fans of modern country music while still doing traditional country music justice, fans will definitely have much more to look forward to from this Florida singer.