On This Day, Aug. 20, 1988: Steve Winwood lands his first and only #1 album, ‘Roll With It’

On This Day, Aug. 20, 1988 …

Former Traffic guitarist Steve Winwood hit #1 on the Billboard 200 Album chart with his fifth studio album, Roll With It. It would be his only #1 album as a solo artist. 

The album’s title track hit #1 on the Billboard Hot 100, where it spent four weeks. It was Winwood’s second and final solo chart-topper. He previously hit #1 with 1986’s “Higher Love.”

Several other singles were released from Roll With It, including “Don’t You Know What the Night Can Do?,” which was featured in a Michelob beer commercial, “Holding On” and “Hearts on Fire.”

The album went on to earn Winwood a Grammy nomination for Album of the Year, while the title track was nominated for Record of the Year and Best Male Pop Performance.

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