In 1992, Kentucky native John Michael Montgomery made his first mark on the country music scene with the release of his debut album Life's a Dance. The record's title track found widespread success, while his followup single "I Love the Way You Love Me" quickly became his first No. 1 hit. The popularity of those songs became the catalyst of a long and impressive career for Montgomery, who has recorded ten studio albums, won multiple CMA and ACM Awards and earned multiple Grammy Award nominations.

He began his career by performing in a band alongside his brother, Eddie Montgomery, and Troy Gentry. Eddie and Troy would later find their own success as country music duo Montgomery Gentry, prior to Troy Gentry's passing in 2017. As a solo artist, John Michael earned accomplishment after accomplishment, including platinum-certified records and a string of hits that span over a decade.

In recent years, John Michael Montgomery has taken a break from releasing his own music but has continued to actively tour. He's even passed the country music baton onto his talented son Walker Montgomery, who The Boot named as an Artist to Watch in 2021.

Now, let's take a look back at some of John Michael Montgomery's best and most beloved tracks, so far.

  • 10

    "Home To You"

    From: 'Home To You' (1999)

    Released in 1999, "Home to You" was the title track of Montgomery's sixth studio album. The song, a sweet ode to long-lasting love, peaked at No. 2 on the country charts.

  • 9

    "Hold On To Me"

    From: 'Leave a Mark' (1998)

    Penned by Blair Daly and Will Rambeaux, "Hold On To Me" is another honest, heartfelt love song that found success on the Billboard charts in 1998.

  • 8

    "The Little Girl"

    From: 'Brand New Me' (2000)

    Montgomery's 2000 single "The Little Girl" marked an important new chapter in the country singer's career. Featuring backing vocals from Alison Krauss and Dan Tyminski, the emotional, heartbreaking story-song became his seventh career No. 1 hit. It held the top spot on Billboard's Hot Country Songs chart for three consecutive weeks.

  • 7

    "I Love The Way You Love Me"

    From: 'Life's a Dance' (1993)

    The second single from Montgomery's debut album Life's a Dance helped launch him from an artist to watch to one of country music's brightest stars. The dramatic, soulful ballad became the first No. 1 single of his career and earned the title of Song of the Year at the 1993 ACM Awards.

  • 6

    "Letters From Home"

    From: 'Letters From Home' (2004)

    The hopeful but poignant single "Letters From Home" tugged at the heartstrings of many Americans in the post-9/11, war dominated social climate of 2004. The song's lyrics tell the story of a soldier writing back to his loved ones back in the U.S. in a simple but incredibly impactful way.

  • 5

    "Life's a Dance"

    From: 'Life's a Dance' (1992)

    The title track and first single of Montgomery's debut album acted as the perfect introduction into the country music scene. Although it only made it to No. 4 on the charts, the heartfelt story-song about the lessons we learn in life helped position him for rapid success with his next single, "I Love the Way You Love Me."

  • 4

    "I Swear"

    From: 'Kickin' It Up' (1994)

    1993's "I Swear" was an unexpected crossover hit for John Michael, hitting No. 1 at country radio and even charting on Billboard's all-genre Hot 100. The song took on a new life the following year when R&B outfit All-4-One recorded their own version of the song. All-4-One earned the Grammy Award for Best Pop Performance by a Duo or Group with Vocal from their recording, and even found additional success with a cover of another one of Montgomery's hits, "I Can Love You Like That."

  • 3

    "Be My Baby Tonight"

    From: 'Kickin' It Up' (1994)

    "Be My Baby Tonight" was the third single from Montgomery's 1994 record Kickin' It Up and became another No. 1 hit. The upbeat, tongue-twisting track immediately connected with fans and still brings folks out onto the dance floor for some boot-scooting.

  • 2

    "I Can Love You Like That"

    From: 'John Michael Montgomery' (1995)

    The first single from Montgomery's 1995 self-titled record, "I Can Love You Like That" is one of his longest-running country radio successes. After a steady climb on the charts for over four months, it hit No. 1 and stayed there for three weeks, only being briefly dethroned by Brooks and Dunn's "Little Miss Honky Tonk."

  • 1

    "Sold" (The Grundy County Auction Incident)

    From: 'John Michael Montgomery' (1995)

    Every successful artist has one song that becomes their trademark hit. "Sold (The Grundy County Auction Incident)" stands as one of the most well-known hits from the 1990s and is often referenced as Montgomery's most recognizable track. The playful tune hit No. 1 on the Billboard charts and became the top-played country song of 1995.

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