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“Roll With It” by Steve Winwood

Updated: Feb 16, 2022

“Roll With It” by Englishman Steve Winwood spent the most weeks at #1 in the United States (4 weeks) in 1988. The song was written by Steve Winwood and American Will Jennings. The writing team of Holland-Dozier-Holland was also credited as co-writers since it resembled the song “(I’m a) Road Runner” by the American band Junior Walker’s and the All Stars. Additional information can be found in the book #1 Singles in the 1980s and on the podcast episode The Top Singles in 1988!

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