On This Day: June 20, 1988 – Steve Winwood Releases Roll with It | We Love the Eighties – 80s Radio, Forums, and Pop Culture Community

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Overview Discussion

Jun 20, 2025

Pete

Mr. Eighties

Pete has published a news story:

On This Day: June 21, 1988 – Steve Winwood Releases Roll with It.

On this day June 21, 1988, Steve Winwood released his fifth solo album Roll with It. Building on the success of his 1986 album Back in the High Life, this release featured a confident blend of blue eyed soul, rock, and rhythm and blues. The title track Roll with It became a major hit, topping the Billboard Hot 100 and driving the album straight to number one on the Billboard 200.

The album eventually sold over 2 million copies in the United States and reinforced Winwood’s role as a major...

Read the full story here...