"Roll with It" is a song recorded by Steve Winwood for his album Roll with It, released on Virgin Records. 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".
The single spent four straight weeks at No. 1 on the Billboard Hot 100 singles chart starting on the issue dating July 30, 1988. It topped the Billboard adult contemporary chart for two weeks, and also spent four weeks at No. 1 on the Billboard mainstream rock chart. In addition, the song reached No. 30 on the R&B chart. In the United Kingdom, the song reached No. 53 on the UK Singles Chart.
"Roll with It" was nominated for two Grammy Awards in 1989, Record of the Year and Best Male Pop Vocal performance. The album Roll with It was also nominated as Album of the Year.
The music video, directed by David Fincher and filmed in sepia-tone, depicts Winwood performing the song in a bar. As he and his band play, bar patrons erotically dance with each other.
7-inch: Virgin / VS 1085 United Kingdom
7-inch: Virgin / 7-99326 United States
12-inch and CD Single: Virgin / VST 1085, VSCD 1085 United Kingdom
12-inch: Virgin / 7 96648-0 United States