"Roll with Me" is a song written by Clint Daniels and Tommy Karlas, and recorded by American country music duo Montgomery Gentry. It was released in August 2008 as the second single from their album Back When I Knew It All. It became their twentieth single to reach the Top 40 on the Billboard Hot Country Songs charts and on the weeks of December 20—27, 2008 has become their fifth Number One song. The song is part of the track list for Now That's What I Call Country Volume 2.