John Michael Montgomery: ‘It’s Been a Pretty Cool Life’

The fall months of 1992 were ones of celebration for John Michael Montgomery. Having just signed a label deal with Atlantic, he was happily watching as his debut single, “Life’s A Dance,” was moving up the singles chart. Looking back, he says that he couldn’t have imagined what was around the corner.

“I think back to when I was just playing honky-tonks in Central Kentucky, and Lexington, I didn’t have a clue what was going to happen. I knew I was going to be picking and singing the rest of my life, whether that was on somebody’s back porch or on the stage,” he reflected to Sounds Like Nashville. “I was fortunate enough to be discovered here in Kentucky, and to be able to come up with a song like ‘Life’s A Dance’ to kick the career off, that’s pretty much how my life was – my dad was a guitar player and singer, and my mom played drums and sang. We moved around a lot. They had a lot of various jobs, because if things interfered with us singing on the weekends, they wouldn’t take it. It was a really cool way of growing up, especially with my brother being a part of Montgomery Gentry, and lightning striking twice. It’s been a pretty cool life, I’ve got to say.”

The single climbed all the way to No. 4 on the charts, and his fan base was growing with each week. He said it was a truly magical time. “There’s nothing like hearing your song on the radio. There’s something that is magical about it. People kept telling me they were hearing my song on the radio, and for the first few weeks, I was the only person who never would hear it. I kept the radio on all the time. I wanted to catch it on the radio so bad.”

As it turned out, while Montgomery’s star was rising, he was also fulfilling his prior booking arrangements he had made before the song was released. “The other funny part to the story was that when the song came out, and it hit the Top-40, then the Top-30, I was still playing the nightclubs in Lexington five nights a week. They’d see me singing and wonder why I was still on the clubs. I had some shows booked off of ‘Life’s A Dance,’ but they weren’t until down the road. I’ve still got to make a living. You could pay five bucks to come in and hear me sing ‘Life’s A Dance.’ A lot of people couldn’t understand that.”

His next single, the romantic ballad “I Love The Way You Love Me,” climbed even higher than “Life’s A Dance” did – all the way to number one in the spring of 1993. He admits to having had a special feeling about the song. “That was the one I wanted to come out with first from the album. The label wanted to come out with ‘Life’s A Dance,’ and they thought it represented me well. I figured they had been in the record-making business longer than I had, so we went with ‘Life’s A Dance,’ and then ‘I Love The Way You Love Me’ came out, and it did everything I thought it would. I loved singing ballads, and growing up listening to Lionel Richie and George Strait, those were my two favorite artists to listen to when it came to romantic songs. I knew what kind of songs I wanted to sing, and I just knew that was going to be my signature song. It went to number one, and I was just so excited to have two hits out. It was a special song to me, being my first number one hit.”

Montgomery stresses that he would have been content with those two hits, but the first single from his 1994 sophomore album Kickin’ It Up would continue the trajectory of his career even higher – “I Swear.” He remembers where he was when he was pitched the song.

“I was on the lake with one of the songwriters, and we were writing together. It was when ‘I Love The Way You Love Me’ was going to be announced as the number one song on the countdown that weekend, and I apologized to him. I was so excited about having the number one single that I didn’t think I’d be able to really write anything,” he recalled. “We had this old cassette player that we were laying down some ideas to, and he pulls out this cassette, and says ‘I wrote this a few years ago, and the publishing company doesn’t push it anymore, but I believe in it still. I think it’s been waiting for the right artist, and I believe that you’re the one. So, he puts it in the cassette player, and I knew I wanted to record it. I told him to send it to my producer, Scott Hendricks. I was out on the road, and he called me and said ‘You gotta get in here and listen to this song.”

The success of “I Swear” kicked his already-growing career into an even faster lane. He says that he wishes he could remember all the high points from that period, but savoring the moment proved to be somewhat difficult. “It was tough to stop and smell the roses. Things were happening so fast for me. I have a one-track mind so I was focused on everything going on in front of me. I knew what was happening, and that it was so cool, but the train was moving so fast. I was enjoying it, but it was hard to take everything in all at once. I tried to enjoy the moment, but it was just tough to do that when things were going fast.”

The song just barely missed the Pop top-40, peaking at No. 42, but a cover from All-4-One hit number one on the Hot 100 and the AC charts. One might have thought that Montgomery felt cheated out of having a much-dreamed-about crossover record, but as it turns out, that was his choice. “I was approached by Rick Blackburn at the label about crossing over. They wanted to take the steel guitar out, and make it more pop. I just told them I really didn’t want to be a crossover artist. I was a Country artist. At that point, I was enjoying as much as I wanted as far as my success went. He said there’s some artists on Atlantic in New York that wanted to release the song, and the label wanted to run it by me. I said ‘Let them go for it. I’m good where I’m at.’ A month or two later, that song came out for All 4 One, and they crushed it. It needed to be a crossover song, I think. I had no regrets.” The cross-over with the pop group happened once more, though in a different way. “With ‘I Can Love You Like That’ it was actually pitched to us both at the same time. We actually both cut the song at the same time, released it at the same time, and it worked for both of us.,” he explained.

With the success of his early ballads, Montgomery’s place in Country Music history, as well as in wedding culture, was firmly cemented. It’s something he takes a lot of pride in today. “One of my all-time favorite songs that I sang in the nightclubs was ‘The Wind Beneath My Wings.’ I always thought if I could ever have a song that was as strong as that one that became a part of someone’s life, I would be very blessed. For me, I wanted to be able to sing songs twenty-five years down the road that still had a big following. To have a song that people included as part of the very special moments of their lives, such as getting married, that means it’s a pretty important song – the kind that you want to have, for sure.”

As the 90’s progressed, Montgomery’s hits went on to include such non-love songs as “I Miss You A Little,” “The Little Girl,” and “Letters From Home.” He says that he always enjoyed coming at fans with new angles in his music. “I think that I have a lot of different sides of me as far as being a singer. I grew up in an era where I would sing anything from Jimmy Buffett to Southern Rock to Merle Haggard. I wrote ‘I Miss You A Little’ when my dad passed away, because it was crushing for me to have him pass away during some of the best times of my life. I wrote that, not necessarily meaning for it to be single, but it was. With ‘The Little Girl’ and ‘Letters From Home,’ I was able to show my storytelling side, and that I wasn’t just a love song singer. It was another dimension that I was able to reach into, and it worked for me. I remember listening to Red Sovine’s ‘Teddy Bear’ as a kid, and having my own CB. I draw off of moments like that growing up on things like The Little Girl. It absolutely tears your heart out, but you can’t stop listening because the story gives you the goosebump factor.”

Montgomery says that there are no current plans for a new album, but there still might be a new project coming soon. “I don’t really have a lot of plans along those lines. We might do a 25th Anniversary album, and throw a couple of new things on it – maybe one with Eddie,” he said, admitting that he is very comfortable to be able to keep taking his music to the people. “I’m enjoying my life getting to go up and down the road singing the hits I was fortunate to have, and the fans still seem to enjoy them. I love being on the road picking and singing – that was always my biggest reason for being in the music business and to be able to get up on stage and sing songs for people is something I am blessed to do.”