Montgomery Gentry's Biggest Billboard Country Chart Hits

The band's Troy Gentry died at age 50 in a helicopter crash on Sept. 8

As the country music community mourns the death of Montgomery Gentry’s Troy Gentry, who died at age 50 in a helicopter crash on Friday (Sept. 8), Billboard remembers the biggest hits of the duo’s career.

Montgomery Gentry, whose name comes from the surnames of members Eddie Montgomery and Troy Gentry, first hit the Billboard charts on Feb. 13, 1999, when “Hillbilly Shoes” debuted at No. 70 on the Hot Country Songs chart. “Shoes” marked the first of the duo’s 28 charted titles and peaked at No. 13 that May.

Less than six months later, in November 1999, the pair claimed its top 10 breakthrough on Hot Country Songs as “Lonely and Gone” sailed to No. 5. Fifteen further top 10 hits followed between 2001 and 2012, including five No. 1s: “If You Ever Stop Loving Me” (one week in 2001), “Something to Be Proud Of” (two weeks, 2005), “Lucky Man” (two weeks, 2007), “Back When I Knew It All” (one week, 2008) and “Roll With Me” (two weeks, 2008).

The latter tune also leads the list of Montgomery Gentry’s biggest hits on the Hot Country Songs chart. Here’s the complete top 10. (For details on how this list was compiled, see below)

Rank, Title, Peak Position, Peak Date
1.“Roll With Me,” No. 1 (two weeks), Dec. 20, 2008
2.“What Do Ya Think About That,” No. 3, Jan. 5, 2008
3.“If You Ever Stop Loving Me,” No. 1 (one week), July 3, 2004
4.“Back When I Knew It All,” No. 1 (one week), July 12, 2008
5.“Lucky Man,” No. 1 (two weeks), July 7, 2007
6.“She Couldn’t Change Me,” No. 2, July 21, 2001
7.“Something to Be Proud Of,” No. 1 (two weeks), Oct. 8, 2005
8.“Gone,” No. 3, April 30, 2005
9.“She Don’t Tell Me To,” No. 5, March 25, 2006
10.“My Town,” No. 5, Nov. 2, 2002

Montgomery Gentry also remained a steady presence on the Top Country Albums chart, with its first nine sets all reaching the chart’s top 10. The streak began with the duo’s 1999 debut, Tattoos & Scars, which peaked at No. 10, and continued through 2011’s Rebels on the Run, which topped out at No. 9. Its most recent album, 2015’s Folks Like Us, debuted and peaked at No. 13.

That run of hit albums has fueled 5.2 million in U.S. album sales through Aug. 31, according to Nielsen Music. In addition, the pair has sold 6.4 million song downloads.

Montgomery Gentry’s Biggest Billboard Hits chart is based on actual performance on Billboard’s weekly Hot Country Songs chart. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at No. 100 earning the least. Due to changes in chart methodology over the years, certain eras are weighted to account for different chart turnover rates over various periods.