The 15 Best Montgomery Gentry Songs, from Hillbilly Shoes to Roll with Me

What is Montgomery Gentry's most famous song?

"Something to Be Proud Of" and "Lucky Man" are Montgomery Gentry's most famous songs, two of their five number one country hits. The others are "If You Ever Stop Loving Me", "Back When I Knew It All" and "Roll with Me", and fans also love "My Town", "Hell Yeah" and "Gone".

Montgomery Gentry's number one songs

1. "If You Ever Stop Loving Me", 2004: their first number one, a heartfelt love song.
2. "Something to Be Proud Of", 2005: a moving song about a father, a son and what makes a life worthwhile.
3. "Lucky Man", 2007: a Grammy-nominated song about counting your blessings.
4. "Back When I Knew It All", 2008: a wry look back at a reckless youth.
5. "Roll with Me", 2008: a tender love song and their fifth number one.

Montgomery Gentry's biggest hits

6. "She Couldn't Change Me", 2001: a number two hit.
7. "Gone", 2005: a hard-charging number three hit.
8. "Hell Yeah", 2003: a rowdy, top five anthem.
9. "My Town", 2002: a proud, top five ode to small-town life.
10. "Speed", 2002: a top five single from the My Town album.
11. "Lonely and Gone", 2000: a top five hit from their debut album.
12. "Where I Come From", 2011: a top ten song of hometown pride.

Early Montgomery Gentry songs

13. "Hillbilly Shoes", 1999: their debut single, a defiant country rocker.
14. "Daddy Won't Sell the Farm", 2000: a top 20 song about holding on to the family land.
15. "Tattoos and Scars", 1999: the title track of their debut album.

Who were Montgomery Gentry?

Eddie Montgomery and Troy Gentry grew up in Kentucky and played the bars and honky-tonks around Lexington, at one point in a band with Eddie's younger brother, the country star John Michael Montgomery. As a duo they released their debut album, Tattoos and Scars, in 1999, and their mix of Southern rock grit, outlaw attitude and heartfelt songs about family and small towns made them one of the most popular duos in country music. They won the Country Music Association's Vocal Duo of the Year award in 2000 and were invited to join the Grand Ole Opry in 2009.

Troy Gentry

On September 8, 2017, Troy Gentry was killed when a helicopter crashed in Medford, New Jersey, shortly before the duo was due to perform there. His death shocked the country music world. Eddie Montgomery has continued to perform the duo's songs, carrying on the Montgomery Gentry name and honoring his partner's memory. For more songs to remember a country fan, see our country funeral songs.

The story behind Something to Be Proud Of

"Something to Be Proud Of", released in 2005, is a story song about fathers, sons and the value of an honest, hardworking life. It became one of their biggest hits and a favorite for graduations, Father's Day and military homecomings, and it is still one of the songs fans most often request in their memory.

Montgomery Gentry albums to start with

• Tattoos and Scars (1999): the debut, with "Hillbilly Shoes" and "Lonely and Gone".
• My Town (2002): with "My Town", "Speed" and "Hell Yeah".
• You Do Your Thing (2004): with "If You Ever Stop Loving Me" and "Something to Be Proud Of".
• Some People Change (2006): with "Lucky Man".
• Back When I Knew It All (2008): with the title track and "Roll with Me".

Country with a Southern rock edge

Montgomery Gentry's sound owed as much to Lynyrd Skynyrd and the Charlie Daniels Band as to Nashville. Loud electric guitars, Eddie Montgomery's gravelly baritone and Troy Gentry's smoother tenor gave their records a rowdy, bar-band energy, while their best songs balanced the party anthems with honest stories about working people, fathers and hometowns. That mix helped pave the way for the rock-flavored country of the 2010s.

Montgomery Gentry songs for a wedding or a dad

"Roll with Me" and "If You Ever Stop Loving Me" are heartfelt first dance choices for a country couple, and "Lucky Man" is a joyful song for an anniversary. "Something to Be Proud Of" is a moving pick for Father's Day or a father-son moment at a wedding. For more, see our country wedding songs and father-son songs.

Montgomery Gentry songs for a party or a road trip

For a tailgate or a drive, play "Hell Yeah", "Gone", "Speed", "Hillbilly Shoes" and "My Town", and finish with "Back When I Knew It All" for a laugh. For more, see our road trip songs and 90s country songs.

More country duos and Southern rock

If you love Montgomery Gentry, explore our Big and Rich songs, Brooks and Dunn songs, Whiskey Myers songs and Gary Allan songs.

A country song about them

Montgomery Gentry sang about hometowns, family and the people who make life worth living. A personalized country song can do the same for someone you love: their name, their hometown and the stories only your family knows. It makes a great Father's Day, birthday or anniversary gift.

How to create a personalized country song

1. Choose a style from 14 genres: country, rock, acoustic and more.
2. Add their name.
3. Share three memories or details about them.
4. Review the lyrics and edit or regenerate them for free before any music is made.
5. Listen to 4 free 45-second previews and choose your favorite.

The full 3 to 4 minute song costs $35.99, or $40.99 for Premium with four full versions and editable lyrics. You get the MP3, a gift page and the lyrics as a PDF.

Give them a country song of their own: create a song and hear four previews for free.