It was written by Winwood and long-time collaborator Will Jennings.

Publishing rights organization BMI later had Motown songwriters Holland-Dozier-Holland credited with co-writing the song due to its resemblance to the Junior Walker hit "(I'm a) Roadrunner".

1 on the Billboard Hot 100 singles chart in the summer of 1988.

"Roll with It" was nominated for two Grammy Awards in 1989, Record of the Year and Best Male Pop Vocal performance.

The music video, directed by David Fincher and filmed in sepia-tone, depicts Winwood performing the song in a bar.