Montgomery has released 10 studio albums. His first seven albums were released via Atlantic Records Nashville, and his next two via parent company Warner Bros. Records Nashville after Atlantic closed its country division in 2001. His first three albums, Life's a Dance (1992), Kickin' It Up (1994), and John Michael Montgomery (1995) are all certified multi-platinum by the Recording Industry Association of America (RIAA); 1996's What I Do the Best is certified platinum; while Leave a Mark (1998) and Brand New Me (2000) are certified gold.
John Michael Montgomery was born in Danville, Kentucky on January 20, 1965 to parents Carol Dean (née Lay) and Harold Edward Montgomery (1941-1994). He was raised in Nicholasville, Kentucky. Montgomery received musical encouragement from his father, who played in a local country band and taught him his first chords. John Michael joined the family band (which included his older brother, Eddie Montgomery, who with Troy Gentry would form the duo Montgomery Gentry), playing guitar before becoming lead singer when his parents divorced. Later, he performed as a solo artist playing "working man's country." Atlantic Records spotted him and signed him.
In 1992, Montgomery's debut album, Life's a Dance, produced his chart debut in its title track, which peaked at number 4 on the Hot Country Songs charts. It was followed by his first number 1 hit, "I Love the Way You Love Me", which also crossed over to the Billboard Hot 100 with a peak of number 60. The album's last single was "Beer and Bones", with a number 21 country peak. "I Love the Way You Love Me" was named Single of the Year by the Academy of Country Music, and Life's a Dance earned triple-platinum Recording Industry Association of America (RIAA) certification for shipments of three million copies. He appeared on the PBS music program Austin City Limits in 1994 during Season 19.
Montgomery's second album was 1994's Kickin' It Up. This album was led off by the No. 1 country and No. 42 pop hit "I Swear", which was also the top country song of 1994 according to Billboard Year-End. After this song came the No. 4 "Rope the Moon", and two more No. 1 singles in "Be My Baby Tonight" and "If You've Got Love". "I Swear" gained further success a year later, when it was covered by pop group All-4-One. Kickin' It Up also sold even higher than his debut, earning a quadruple platinum certification for shipments of four million copies.
In 1995, he released his self-titled third studio album. Also a quadruple-platinum seller, it accounted for five hit singles, including the Number One hits "I Can Love You Like That" and "Sold (The Grundy County Auction Incident)". Like "I Swear" before it, the former was covered by All-4-One, while the latter was also declared the Number One country hit of 1995 on the Billboard Year-End charts. After this pair of Number One hits came the No. 3 "No Man's Land", then two consecutive No. 4 singles in "Cowboy Love" and "Long as I Live." Also included on the album was "Holdin' Onto Somethin'", which was a top 10 country hit in early 1996 for Jeff Carson. At the end of 1995, Montgomery placed his career on hiatus due to a vocal cord injury.
What I Do the Best was his fourth studio album, released by Atlantic in 1996. This was the first album of his career not to produce a No. 1 country hit. It also failed to match the sales of its predecessors, although it still earned platinum certification. This album was led off by the No. 15 "Ain't Got Nothin' On Us", which despite debuting in the Top 40 its first week on the charts, also became his first single since 1993's "Beer and Bones" to miss Top Ten. He regained his chart momentum with three more Top Ten hits off the same album: "Friends" at No. 2, "I Miss You a Little" at No. 6 and "How Was I to Know" also at No. 2. After this album, he released a Greatest Hits album in 1997, which reprised his greatest hits to that point and went platinum in the United States. It also included the new song "Angel in My Eyes", which was a No. 4 single for him that year. Also in 1997, Montgomery sang guest vocals on "Warning Signs", a No. 56-peaking musical track which included snippets from a Bill Engvall comedy sketch.
In 1998, Montgomery released his fifth album, Leave a Mark. This album contained a more pop-oriented sound than his previous work. Despite only earning a gold certification from the RIAA, it accounted for three more hit singles. First was "Love Working on You" at No. 14, followed by "Cover You in Kisses" at No. 3 and "Hold On to Me" at No. 4. Despite having several of his singles cross over to the pop charts, "Hold On to Me" was his first Top 40 pop hit, reaching No. 33 on the Hot 100.