John Michael Montgomery’s last dance: Country star ends touring with Rupp finale

Retirement didn’t specifically spring from the event, but when John Michael Montgomery’s bus crashed and overturned en route to a North Carolina concert in 2022, the idea of giving up the road took on a pronounced appeal.

“Totaled the bus. Broke some ribs. I was looking through a broken windshield at I-75 going, ‘I’m getting too old for this.’”

The Danville -born, Nicholasville-raised, Lexington-schooled singer — a Grammy nominated, multiple platinum-selling presence on country radio for more than three decades — said having his tour bus doing somersaults on the interstate isn’t the reason he is giving up touring. The incident stands as but one chapter in an extensive career that has offered immeasurable fortunes. But it has also worn him down.

This weekend, 33 years after “Life’s a Dance” introduced him to country audiences in a huge way, Montgomery is getting off the bus. His Friday concert will be his last official tour date.

“It’s just one of those things,” Montgomery said. “You wake up like any pro athlete would do and one day you look in the mirror and go, ‘Man, this is a young man’s game.’

“It’s bittersweet. It’s kind of surreal because, well, it’s been 33 years. I just turned 60 this year. And I listen to this 60-year-old body. I came to this realization about five years ago when COVID came in and shut down the whole music industry. That’s the first time I hadn’t been on a bus or toured or been traveling in almost 30 years. I just remember at the end of that year how good my body felt. Everything was rested — my voice, my body. I was like, ‘Wow, I didn’t realize how hard traveling was starting to be on me,’ so I cut shows back from 70 shows a year to about 30 to 25 shows a year.

“Before COVID, I used to get out there and go up and down the road. You don’t realize, as you’re getting older, how much wear and tear you’re getting on you. That’s when I really started thinking about it. Then I had the bus wreck. I’ve just come to terms with it all over the last year. I’ve had a great, great, wonderful career and everything, but I was like ‘I think it’s time to hang up the ol’ boots, get off the road, quit touring and rest my body.’”

Remembering his first Rupp gig

Having the road end at Rupp for Montgomery is fitting as the arena has been his home state performance haven ever since “Life’s a Dance,” the singer’s debut single, became a Top 5 hit. His debut performance there came in January 1993 as a featured entertainer at a truck pull (“Oh man, I forgot about that.”)

He returned in September 1994 as show opener for Reba McEntire with five No. 1 singles to showcase (including “I Love the Way You Love Me” and “I Swear.”) From 1996 onward, Montgomery played Rupp as a headliner.

“As I was growing up, Rupp Arena was the ultimate place,” Montgomery said. “I went to concerts there in the ’80s. I saw everybody from ZZ Top to Journey to Alabama. With Alabama, I was like, ‘Wow. A country music artist is headlining Rupp Arena? I mean, you just didn’t see that. Of course, Randy Travis came out not long after that. I remember when he came in and packed the place. I never thought I would see country music so popular that it could sell out Rupp Arena. I was a young teenager at that point and was just amazed by the place. And, of course, there was basketball. I never dreamed I would ever do a concert there myself. Rupp Arena, to me, has just always been the greatest venue ever. It’s such a special place.

“So, for the last show in my last year of touring, the booking agency said, ‘Hey, what do you think about finishing at Rupp Arena at the end of the year? I went, ‘Let’s go for it.’”

Performing with Montgomery family

Of course, as any longstanding Central Kentucky fan of Montgomery will readily acknowledge, the singer had a full career in progress long before the rest of the country heard his music. Having cut his musical teeth in bands led by father Harold Montgomery, a young John Michael found himself playing five nights a week at the still-active-today Austin City Saloon in Woodhill Center. Backing him were brother Eddie Montgomery and singer Troy Gentry. Both would eventually find their own stardom and headline their own Rupp concerts as Montgomery Gentry (Eddie Montgomery will be also be part of Friday’s show along with John Michael’s son Walker Montgomery and son-in-law Travis Denning.)

“Back at the Austin City Saloon, it was me, Eddie, Troy and a couple other guys all doing our thing five nights a week. Living it up as a house band in Lexington ... I mean, we thought that was the ultimate gig. Little did I know that a few years later, I would be on Atlantic Records.

“All of that was actually the result of a lucky situation because the guys from Atlantic had come to town to see another singer. One of them said, ‘Well, we were here checking this other singer out and the waitress said, ‘You need to go down the road to this place called Austin City Saloon and listen to this guy John Michael Montgomery. So, thanks to her, whoever she was ... I mean, she got me the record deal. If I ever figure out who she was, I’ll give a big tip.”

Standout career moments for Montgomery

After three-plus decades as a major league country artist, does any single event stand as a career highlight for the soon-to-be retired Montgomery?

“Having a No. 1 record is every singer’s dream. I really wanted ‘I Love the Way You Love Me’ to come out first, but the label said, ‘No, we don’t want to put out a four-minute ballad as your first single. You’re a new artist. We’re going to go with ‘Life’s a Dance.’ It’s mid-tempo and we think people will love it.’ And it ended up going Top 4. Then ‘I Love the Way You Love Me’ came out and ended up being my very first No. 1 hit.

“I tell you, there was no better feeling than to hear Bob Kingsley on American Country Countdown say my name. ‘Our new No. 1 this week is by ...’ That was just an unbelievable feeling. It was something you never dream would happen to a local boy growing up playing music with his mom and dad and brothers on the front porch or on a weekend somewhere at a VFW. You just never think it’s going to happen to you, let alone get you a record deal.

“At that point, I thought, ‘I have a No. 1 hit record and nobody can ever take that away from me. That means I won’t have to actually find a real job.’”

John Michael Montgomery – The Road Home: The Final Concert with Walker Montgomery, Montgomery Gentry featuring Eddie Montgomery and Travis Denning

When: Dec. 12 at 7 p.m.

Where: Rupp Arena, 430 W. Vine

Tickets: $29.75-$129.55 through ticketmaster.com.