On This Day, July 30, 1988: Steve Winwood hit #1 with ‘Roll With It’

By Jill Lances

July 30, 2025 at 11:00 am EDT

On This Day, July 30, 1988 ...

Former Traffic star Steve Winwood topped the Billboard Hot 100 chart with "Roll With It," the title track from his fifth studio album.

The track spent four weeks in the top spot and was one of two #1 hits Winwood would have during his solo career. The other was “Higher Love,” which topped the chart in August 1986.

While Winwood wrote "Roll With It" with Will Jennings, the performing rights organization BMI later gave the Motown songwriting team of Holland-Dozier-Holland – Lamont Dozier and brothers Brian Holland and Eddie Holland – credit, due to the song's similarity to "(I'm a) Roadrunner," which they wrote for Junior Walker.

“Roll With It” went on to earn Grammy nominations for record of the year and best male pop vocal performance. The album was also nominated for album of the year.