Goin’ Once, Goin’ Twice, Sold: On John Michael Montgomery’s Self-Titled Smash Hit

On June 16, 2022

It’s the kind of fact you discover via a late night TikTok scroll, or one of those vacuous #MusicFacts Twitter accounts that remind you that, on this date, the Beatles recorded “I Am the Walrus.” In a previous generation, it’d been conveyed via VH1’s Pop-Up Video. But the fact remains intriguing and inconceivable in any era: In 1994 and 1995: the country singer John Michael Montgomery and the R&B/pop group All-4-One had simultaneous cross-chart Billboard hits with the same two songs, “I Swear” and “I Can Love You Like That.” While previous generations of chart gamery included semi-simultaneous covers — look to the album cuts of every Motown record until What’s Going On, especially — no one had ever hit upon the ingenious, and possibly amoral, technique of taking two invincible ballads, and tweaking the musical formula to include more drums (All-4-One) or more twang (JMM). This was not a cover of “All Along the Watchtower” by an artist played on the same radio station, coming mere months after the original; this was a concerted effort by the A&R staff at Atlantic Records to seed the same song to two different genres, to see if both could become hits. 

What’s even crazier than this strategy being attempted in the first place is that it worked. It worked almost too well. “I Swear” was first, and while All-4-One’s went to No. 1 on the Hot 100, John Michael Montgomery’s was No. 1 one on the Country chart and No. 42 on the Hot 100. The centerpiece single for Montgomery’s self-titled third album that appears on vinyl here for the first time, “I Can Love You Like That” went to No. 1 on the Country chart a year later, while All-4-One’s went to No. 5 on the Hot 100. They’d serve as both acts’ commercial peak, Montgomery serving as maybe the only country singer on earth whose fortunes were so closely tied to a ’90s boy band. 

This chart gamesmanship, this breaking down of walls, was another battle of the Country Crossover war, a different flavor of the “Is this country?” battles that would confront Sam Hunt 20 years later, Shania Twain two years later, Garth Brooks five years earlier, Dolly Parton 15 years earlier when she was making disco records and Waylon Jennings 25 years earlier when he was melding rock attitudes to country music. You get the point. But the SoundScan revolution in 1991 changed the game. Essentially, stores scanning UPCs actually applied to the Billboard charts for the first time, giving an actual representation of the tastes of the U.S. record-buying populace vs. the word of record store keepers, like before. The wall between pop, country, R&B and basically every genre became as thin as rice paper.   

The accurate counting of country fans relative to fans of pop, rock and hip-hop also revealed that the country audience was much bigger than anyone would previously acknowledge. It wasn’t just farmers or “hicks” listening to country; it was suburban moms, it was urban professionals, it was people whose hands would never work an acre or milk a cow that were catapulting ’90s country stars to the top of the Billboard pop charts. The music might have started on prairies or in the hills, but it was ending up on the paved subdivisions and big-box retail stores of the suburbs. With this realization of a “new” audience — country had been trying to appeal to the suburbs since “countrypolitan” made outlaws of Waylon and Willie — came a new style of country music, one that was smoother, concerned with the everyday realities of the “normal” people who made up country’s audience, leading to an Urban Cowboy less like a John Travolta character and more a mode for an entertainer to embody.   

At the center of all these storylines is John Michael Montgomery, one of the biggest country albums of the mid-’90s, a commercial behemoth crossover that opened up country’s big tent, headlined by one of the most earnest balladeers country music has ever seen. A Kentucky boy with a big voice, impeccable phrasing and promises of devotion. An unassuming performer whose biggest songs made him — and an R&B group — superstars.

Like many of the greats, Montgomery got his start in the family band, playing alongside his parents, Harold and Snookie, and his siblings. When his parents divorced, his dad kept at it, with young John Michael singing and his older brother Eddie playing drums. The family band never made much money, and the Montgomerys moved frequently, having just enough to feed and clothe the family. Despite the hardship, John Michael and Eddie would both risk it all and follow their parents into music, first in a series of bands with their friend Troy Gentry, and then apart, after John Michael was signed by an Atlantic talent scout looking for the label’s answer to Garth Brooks. Eddie Montgomery and Troy Gentry would form Montgomery Gentry, and become one of country’s most iconic duos, but that would be almost a decade after John Michael, against all odds, actually became the superstar Atlantic was looking for.  

But first, John Michael struggled; even after signing his first deal, he often had to sleep in his car and couldn’t rustle up money to attend concerts, or do much of anything. It was his lean period, but he never wavered. When he finally hit the studio to record Life’s A Dance in 1992, he arrived fully formed. Listening to that album now, it’s especially intriguing to note how much it predicts which direction country music was headed in the ’90s — big, loud ballads paired with fast-paced honky tonk jams — and how crystalized John Michael Montgomery was as a vocalist. He sang from his chest, rattling off runs and big notes like they came directly out of his aorta and right ventricle. The songs he sang were filled with bon mots that would knock you out if the guy down the bar from you had said them at 3 a.m. “Life’s a dance, you learn as you go / Sometimes you lead, sometimes you follow.” That single quote would have been on every conceivable piece of soft goods you could imagine if that song came out today. Life’s a Dance was an instant smash, spawned a No. 1 hit (“I Love The Way You Love Me,” which was covered by an Irish boy band six years later, as tended to happen with Montgomery songs), went Triple Platinum and set Montgomery up as one of country’s biggest stars. 

His stardom tripled, or quadrupled, when his sophomore album, Kickin’ It Up, was the No. 1 album in America in 1994. Powered by “I Swear,” it was the kind of smash Garth Brooks had proven was possible for a country artist, cementing Montgomery’s staying power, and featuring immortal singles like the underrated “Rope the Moon” and the tongue-twister karaoke bar classic “Be My Baby Tonight.”    

By the end of 1994, Montgomery was on top of the country world, one of the genre’s biggest stars and one of music’s most known entities, thanks to “I Swear.” By the end of 1995, he’d have burnt-out vocal cords that required a potentially career-threatening surgery, and another Top 5 LP, John Michael Montgomery.

Coming off the “I Swear” juggernaut, the first single from John Michael Montgomery was released in February, 1995, “I Can Love You Like That.” The song was a hit across two different genres for a reason: It’s as perfectly constructed as a designer watch, with its pre-choruses like the lead-up to a fireworks show grand finale and its tumbling sentences of devotion direct and open, allowing both Montgomery and the All-4-One members to put their own sauce all over it. Montgomery’s version feels, to modern ears, like the more lasting single; he’s more in the pocket of the martial beat behind him, and his key change in the final third is ready-made for car sing-alongs. Within eight weeks, it’d be the No. 1 country song in America, a favorite of sensitive ’90s kids in the back of their parents’ minivans, and the parents driving them. 

John Michael Montgomery was released on March 28, 1995. Its 10 songs are split evenly between Montgomery’s two primary modes: the balladeer and the honky tonk hero who can rattle off lyrics like an auctioneer let loose in a recording studio. Included in the latter is the album’s second single, and second country No. 1, “Sold (The Grundy County Auction Incident).” Montgomery plays the role of a love-struck dummy who sees a woman in the second row of the country auction and has to stand up and declare his love in an auctioneer’s patter. It’s a song that seems technically impossible until you realize you’re hearing it; most people can’t even think as fast as Montgomery sings on “Sold.” It seems like a fever dream now, but “Sold” came at a perfect time. The character of the auctioneer was “having a moment,” as they say; it seemed like most sitcoms in the ’90s had an episode where some mishap happened thanks to a character not following the auctioneer’s action. 

The album’s third single was the mid-tempo ballad “No Man’s Land,” a song that captures so much of what made Montgomery a superstar. His childhood meant that he could credibly sing songs like this one, which centers around a single mom trying to put food on the table with no man helping her. Salient lines like “It’s hard to hold down the fort when you’re holdin down a job / she’d rob Peter to pay Paul, but he’s already been robbed,” were not as present on the “Achy Breaky Heart” landscape of ’90s country, but thanks to artists like Montgomery — and, it’s worth mentioning again, Garth Brooks — the concerns of the everyday people who liked country music became the main concerns of the genre’s songs. 

And because the average country listener of the ’90s was an urbane professional, most likely in a committed relationship, mid-’90s country fans wanted and expected songs of commitment and domestic marital bliss. As such, John Michael Montgomery is largely not an album of heartbreak or of relationship strife. It features no songs about losing his woman, his dog and his truck, as the cliché goes. This is happily married music for happily married — or at least firmly in love — people. Beyond the two smash singles (both ending in happiness, even the one that starts at an auction), there’s “High School Heart,” a song in the mode of the ’80s hair metal ballad that country ballads largely replaced post-grunge, that addresses a high school sweetheart love affair a decade after graduation. “Heaven Sent Me You” imagines divine providence in a long relationship, and “Long As I Live” is a promise to a partner to give every breath to them. And even the song about chasing a woman leaving him in heartbreak — “Holdin’ On To Something” — is mostly bemused as opposed to forlorn. If the audience for country was widening in 1995, it was also settling down: less “Mammas Don’t Let Your Babies Grow Up To Be Cowboys” and more “Mammas Don’t Let Your Babies Grow Up To Be Cheaters.”   

If there was something that set John Michael Montgomery apart from the country stars of the past — beyond his willingness to sing songs that would eventually be bigger R&B hits — it was that he seemed so well-adjusted. There was no fall from grace, no random acts of public intoxication, no public flameouts. Just a regular guy from Kentucky who loved to sing who got to be, briefly, one of the biggest country stars of an entire era. He believed every word he ever sang, earnestly and uncomplicatedly. His era wasn’t Bro Country, it was Guy Country: a whole generation of performers — everyone from Randy Travis to Toby Keith — who went from being just regular guys to being stars. John Michael Montgomery was the No. 1 country album in America for 13 weeks in 1995, more than doubling the time at No. 1 of his previous album, and beating out another ascending country star of 1995 who’d bend the bounds of country stardom in a more substantial way (and whose The Woman in Me held the top spot for 11 weeks): Shania Twain. 

John Michael Montgomery would be Montgomery’s final bow at the top of the country charts, however. Right as his ascendance to the throne happened, he was forced to put his career on pause in late 1995 due to polyps developing on his vocal cords. He had to take an even longer time off in the 2010s for the same issue, but it’s hard to not see the pause in 1995 as a momentum shifter. His next album, 1996’s What I Do The Best didn’t live up to the title, and his subsequent albums haven’t had the same panache, the same ace song selection that made John Michael Montgomery and Kickin’ It Up into smashes. He had a couple more Gold records, but none lived up to the artistic or commercial peaks of his 1994-’95 run. All-4-One, for their part, were never again as big a concern as they were when doing double duty with Montgomery, either.

Remembrances of ’90s country largely reduce the genre to the twin pillars of Garth and Shania, with a wholesale writing-off of the artists who made the genre as commercially successful as pop in the early-to-mid ’90s. And while it might not be the most beloved period among country connoisseurs — the 2010s and the ’70s seem to be the ordained decades — the era’s artists are worthy of reappraisal, its albums way more charming and enduring than they’ve been given credit for. John Michael Montgomery is a symbol of an era, but it’s also 10 songs of earnest, open and, most importantly, fun country music that you can absolutely love like that. 


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Andrew Winistorfer

Andrew Winistorfer is VMP’s Classics & Country Director and a writer and editor of their books, 100 Albums You Need in Your Collection and The Best Record Stores in the United States. He’s written Listening Notes for more than 20 VMP releases, co-produced VMP Anthologies The Story of Philadelphia International Records, The Story of Quincy Jones, The Story of Impulse and the VMP Classics release of Nat Turner Rebellion's Laugh to Keep From Crying, and executive produced The Story of Vanguard and The Story of Willie Nelson. He lives in Saint Paul, Minnesota.

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