Every No. 1 Single of the Nineties: John Michael Montgomery, “How Was I to Know”

“How Was I to Know””

John Michael Montgomery

Written by Blair Daly and Will Rambeaux

Radio & Records

#1 (1 week)

September 12, 1997

John Michael Montgomery’s final No. 1 single of the decade takes him out on a high note.

The Road to No. 1

This was the third consecutive No. 1 single from What I Do the Best, following “Friends” and “I Miss You a Little.”

The No. 1

This is so much better than most of his earlier ballads that it’s almost ridiculous.

The record has actual atmosphere, with a warm Spanish-influenced arrangement that replaces the antiseptic arrangements of the past with real intimacy.

Montgomery also pushes himself further as a vocalist on this track than he ever had before, and he pulls it off.  There’s a beautiful melody here and he nails it.

Collectively, the three No. 1 singles from What I Do the Best make up the best run of his entire catalog.  It’s a shame that it wasn’t enough to maintain his status as a multi-platinum artist.

The Road From No. 1

Montgomery followed “How Was I to Know” with “Angel in My Eyes,” a top five single from his Greatest Hits collection.  His next set, Leave a Mark, produced the top five hits “Cover You in Kisses” and “Hold On to Me,” as well as the top fifteen hit “Love Workin’ On You.”  He finished out the decade with Home to You, which included the top five title track and the top fifteen hit “Hello L.O.V.E.”  We’ll see Montgomery once when we get to the 2000s, as he scores his final No. 1 hit during that decade.

“How Was I to Know” gets an A.

Every No. 1 Single of the Nineties

Previous: Alan Jackson, “There Goes” |

Next: Collin Raye, “What the Heart Wants”


  1. Couldn’t agree any more! I’ve always felt this was seriously one of JMM’s most underrated and often overlooked ballads, despite it being a hit. I personally enjoy this one more than many of his better known ballads, and it’s one of my most played JMM songs on my itunes. Switching to Csaba Petocz as his producer was one of the best moves he ever made in his career, imo.

    “How Was I To Know” to me has much more personality and unique atmosphere than most of the ballads on his last two albums combined. Not to mention, it’s also aged quite well. I especially love how he started showing off his falsetto here, which compliments the beautiful melody in the chorus so well. I personally consider this to be both his most ambitious and one of his best ever vocal performances. I also love the dark and moody style of the lead guitar here, which reminds me of a lot of the Roy Orbison influenced style of country that was coming out of Nashville throughout the mid-late 90’s. It seems like nearly every artist recording in Nashville at that time had their turn at tipping their hat to the “Man In Shades”, and this was JMM’s turn. I also find the lyrics about a man who finally finds the love of his life after thinking the odds were stacked against him for so long to be sweet.

    I also really love the music video with its dim candlelight atmosphere and beautiful location which was an absolute perfect match for the song. Even the tuxedo Montgomery is sporting here compliments the song’s sophisticated, elegant style. I know I’ve probably already said this elsewhere, but man, I really miss when country music was this classy! :) I actually do remember seeing this video on GAC back in 1997, as well, but it didn’t get played quite as much as most of the other then current videos at the time. I especially remember the blonde occasionally seen passing through the hall. Btw, I’ve always wondered why this was his only 90’s music video that was mysteriously omitted from his video hits collection DVD.

    This is yet another song, in which as soon as the first note comes on, it reminds me of the trip to Maine my parents and I went on in the late Summer of 1997. It especially brings to mind when we hung around the South Portland area and stayed at the Hampton Inn located close to the Maine Mall. Again, this song, with it’s dark and moody atmosphere was a perfect fit for the beautiful and mostly cooler, overcast days we experienced while up there. :) When we returned to Maine in the late 2000’s and again stayed at the Hampton Inn in South Portland, both this song and Garth & Trisha’s “In Another’s Eyes” came to mind right away.

    “How Was I To Know” also brings back great memories from the Fall of 1997 when I was just starting 6th grade and middle school. I especially remember hearing it on the radio in my dad’s car one late cloudy afternoon after he had taken me to Best Buy where I always loved to play Diddy Kong Racing, which was the latest Nintendo 64 game I was really getting into. :) “How Was I To Know” was playing just when dad and I had gotten in the car and we were leaving the parking lot of Best Buy, and I was still thinking about the game. Finally, this song also brings to mind when my parents and I started going to Fair Oaks Mall in Fairfax, VA almost every Sunday during the Fall of ’97. Fair Oaks was the closet we ever got to regularly going to a more “upscale” mall around our area. Again, even as recently as the mid 2010’s, this is one song that always came to mind whenever we went back there. I even had it on the late 90’s/early 00’s country playlist I always loved to listen to while walking and shopping around Fair Oaks. :)

    It’s too bad this ended up being Montgomery’s last number one of the decade, because I also love quite a few of his other late 90’s releases like “Angel In My Eyes,” “Cover You In Kisses,” “Hold On To Me,” “Hello L-O-V-E,” and “Home To You.” I especially like how JMM continued to use his falsetto on “Angel In My Eyes” and “Hold On To Me.”

    – “Cover You In kisses” is another one of my personal favorites from Montgomery that seems often overlooked today. I love the Wintery imagery and the cozy atmosphere that both its lyrics and the warm production help create. It also brings back great memories from the Fall of 1998 when I was just starting 7th grade. Oh, and it also gets bonus points for being a Jerry Kilgore co-write. :)

    – “Home To You” is another one of my all time favorites from it’s beautiful melody, the warm, cozy production style from Garth Fundis, and the wonderful memories it brings back for me from the Millennium/Y2k era. The lyrics about being able to come home to your “best friend” after getting “kicked around” always resonated with me, as well, especially after some of my rougher school days later on.

  2. I am really surprised by how much more I am now enjoying Montgomery’s output from this era then I actually did back in 1997. To be honest, I was likely ignoring him and unfairly dismissing his music based upon my initial negative reactions to his earliest material. It’s great to be able to challenge “yesterday me” and my own unreliable history/opinions of these artists.

    This song is rich and atmospheric, moody. Montgomery gives the lie to me belief he was a flat, unskilled vocalist.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.