‘Roll With It’: Steve Winwood Rolls Towards A Double No.1 In The US

The British singer-songwriter, keyboard player and guitarist ruled America in August 1988 with both the ‘Roll With It’ single and album.

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Steve Winwood 'Roll With It' artwork - Courtesy: UMG
Steve Winwood 'Roll With It' artwork - Courtesy: UMG

British rhythm and blues heritage upstaged American rock on August 20, 1988, as Steve Winwood outsold Guns N’ Roses. Roll With It ended the five-week run of Appetite For Destruction on the American album chart for that week. It completed an amazing double victory for the British singer-songwriter, keyboard player and guitarist, who was already at No.1 on the Hot 100 with the single of the same name.

The former member of Traffic and Blind Faith had been growing into a huge solo star, especially in the US, throughout the 1980s. The 1981 set Arc Of A Diver went platinum, as did the 1987 compilation Chronicles. The scene for his latest triumph was really set when 1986’s Back In The High Life, featuring guest appearances by Chaka Khan, James Taylor and others, became a triple platinum sensation.

Steve already had a quarter-century in the business to his name by this time, despite still only being a mere 40 years of age. Roll With It signalled a return to Winwood’s R&B roots with the Spencer Davis Group, and was helped on its way to the top of the chart by the powerfully nostalgic sound of its title track single.

Steve Winwood - Roll With It

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Wearing its Motown influences (and especially those of Jr. Walker & the Allstars) clearly on its sleeve, “Roll With It” had been all over US pop radio all summer. In 1990, the famous label sued Winwood for copyright infringement, citing the song’s close similarity to Walker’s 1966 hit “(I’m A) Roadrunner.” That song’s writers, Holland-Dozier-Holland, were subsequently added to the names of Winwood and Will Jennings as composers of the new hit.

Listen to the best of Steve Winwood on Apple Music and Spotify. 

The single and the album, which both won Grammy nominations, were infused with the soulful sound of the much-travelled Memphis Horns, who had met Winwood while touring with Jimmy Buffett. “It sounds like a combination of old R&B records,” the Memphis Horns’ Andrew Love told writer Robert Gordon. “[It] sounds like ‘Shotgun,’ sounds like the Jr. Walker song ‘Roadrunner.’ We got through putting some Sam and Dave licks on there and some old Stax, Memphis licks and it all came together.”

Buy or stream the Roll With It album.



  1. geoff gladwin

    August 20, 2014 at 6:04 pm

    Rock n Roll….not available in South Africa….

  2. Carolyn Dunn

    August 20, 2014 at 9:18 pm

    I love Stevie Winwood!

  3. Bill varraso

    August 21, 2019 at 2:46 pm

    Grew up on traffic and blind faith .great musician.

  4. Silverback

    April 10, 2023 at 5:50 am

    This album was part of the “One-two” punch Winwood delivered with Back in the Highlife then Roll with it. These Singles and Albums both were incredible back in the 1980’s. I’ll never forget them.

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