"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 songwriter 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 weeks at No. 1 on the Billboard Hot 100 singles chart in the summer of 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.

The song "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.