Montgomery Gentry Is No. 1 Again!! Montgomery Gentry has just hit No. 1 on the country singles chart with “Roll With Me.” This is their 5th No. 1 single and the first time in their careers that they’ve had back-to-back No. 1’s!!! “Back When I Knew It All” hit No. 1 on the country charts this summer. Congrats to the boys of MG – this is a great accomplishment!