"Roll with Me" is the title of a song recorded by the American country music

Country music

Country music is a popular American musical style that began in the rural Southern United States in the 1920s. It takes its roots from Western cowboy and folk music...

 duo Montgomery Gentry

Montgomery Gentry

Montgomery Gentry is an American country music duo composed of vocalists Eddie Montgomery and Troy Gentry. The two began performing in the 1990s as part of a band which also included Eddie Montgomery's brother John Michael Montgomery, and founded the existing duo in 1999.Signed to Columbia Records,...

. It is the second single from their 2008 album Back When I Knew It All

Back When I Knew It All

Back When I Knew It All is the sixth studio album by the American country music duo Montgomery Gentry. It was released by Columbia Records Nashville on June 10, 2008 . The album's title track, which is also its lead-off single, became their fourth Number One on the Billboard Hot Country Songs...

. It has become their twentieth single to reach the Top 40 on the Billboard

Billboard (magazine)

Billboard is a weekly American magazine devoted to the music industry, and is one of the oldest trade magazines in the world. It maintains several internationally recognized music charts that track the most popular songs and albums in various categories on a weekly basis...

Hot Country Songs

Hot Country Songs

Hot Country Songs is a chart published weekly by Billboard magazine in the United States.This 60-position chart lists the most popular country music songs, calculated weekly mostly by airplay and occasionally commercial sales...

 charts and on the weeks of December 20—27, 2008 has become their fifth Number One song.

The song is part of the tracklist for Now That's What I Call Country Volume 2

Now That's What I Call Country Volume 2

Now That's What I Call Country Volume 2 is the second country music compilation album from the Now! series, released on August 25, 2009....

.

Content

The song is a mid-tempo ballad, featuring lead vocals from Troy Gentry and background vocals from Five for Fighting

Five for Fighting

Five for Fighting is the stage name of American singer-songwriter John Ondrasik. He is best known for his piano-based rock, such as the Top 40 songs "Superman " , "100 Years" , and "The Riddle" .-Early years:...

. In it, the narrator sings about taking lyrical inspiration from the world around him, and learning the life lessons about which he sings. This sentiment is reflected in the lines "I'm thinking it's time to be livin' the rhyme / When I'm singing a song about nothing but right / And it'd sure be nice if you would roll with me."

According to Country Weekly

Country Weekly

Country Weekly is an American tabloid style weekly magazine established in 1994. The magazine focuses on country music stars and events, and regularly features exclusive interviews with recording artists and country music news...

, songwriter Tommy Karlas wrote the song after he could not sleep due to insomnia

Insomnia

Insomnia is most often defined by an individual's report of sleeping difficulties. While the term is sometimes used in sleep literature to describe a disorder demonstrated by polysomnographic evidence of disturbed sleep, insomnia is often defined as a positive response to either of two questions:...

. He got together with fellow songwriter Clint Daniels

Clint Daniels

Clint Allen Daniels is an American country music artist. Signed to Arista Nashville in 1998, Daniels released his self-titled debut album that year and charted two singles for Daniels on the Hot Country Songs charts. In 2003, Daniels signed to Epic Records, releasing a third single but no album...

 to finish it. Karlas added the second verse when he thought about a high school friend who had died.

Montgomery Gentry released a rap remix with country-rapper Colt Ford

Colt Ford

Jason Farris Brown known professionally as Colt Ford, is an American country music artist and former professional golfer. He has released three albums via his own Average Joe's label, and has charted four singles on the Hot Country Songs charts...

 as well.

Reception

Eddie Montgomery, the other half of the duo, said of the song: "It's got the groove factor; it's just unreal. I think it's the best performance I've ever heard from my brother over here. Emotionally, you can tell when he sings it, it's from the heart."

Reviewing the song for Country Universe, critic Leeann Ward gave the song a C rating. She considered the lyrics cliché and nonsensical but called the melody "rather pleasant sounding". Thom Jurek of Allmusic considered it "obligatory" and "spiritually minded".

Music video

The music video

Music video

A music video or song video is a short film integrating a song and imagery, produced for promotional or artistic purposes. Modern music videos are primarily made and used as a marketing device intended to promote the sale of music recordings...

, directed by Steven L. Weaver, features stop motion

Stop motion

Stop motion is an animation technique to make a physically manipulated object appear to move on its own. The object is moved in small increments between individually photographed frames, creating the illusion of movement when the series of frames is played as a continuous sequence...

 animation. An interactive version of the video was also posted on the website Hear Something Country, presenting a 360-degree view of the video. The video features Glee

Glee (TV series)

Glee is an American musical comedy-drama television series that airs on Fox in the United States, and on GlobalTV in Canada. It focuses on the high school glee club New Directions competing on the show choir competition circuit, while its members deal with relationships, sexuality and social issues...

 actor Darren Criss

Darren Criss

Darren Everett Criss is an American actor, singer-songwriter, musician, composer, and a founding member and co-owner of the theater company StarKid Productions. He currently portrays Blaine Anderson, an openly gay high school student, on the FOX television series Glee...

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Chart performance

For the week of December 20, 2008, the song became their second consecutive and fifth overall number one hit, where it remained on top for two weeks. It also has become their second Top 40 hit on the Billboard Hot 100, peaking at number 33.

Chart (2008)	Peak position