Roll With It – Steve Winwood | Top 40 Chart Performance, Story and Song Meaning

Chart Performance: Pop (#1 for 4 weeks); 1988

Story Behind The Song By Ed Osborne

If Roll With It reminds you of records such as Shotgun by Junior Walker, there’s a reason. In 1987, England-born Steve Winwood moved to Tennessee, and began exploring the R&B music of the American South.

Although recorded in Toronto, the track featured the wailing trumpet and sax of Wayne Jackson and Andrew Love – a.k.a. the Memphis Horns – who played on many classic soul records.

The song itself was co-written by Will Jennings, who had previously worked with Winwood on While You See A Chance (#7; 1981) and Higher Love (#1; 1996). For his part, Steve turned in a gutsy performance reminiscent of his early days fronting the Spencer Davis Group (Gimme Some Lovin’, #7; 1967).

Roll With It lived up to its title, taking over the top slot for four weeks and for 1988. As for Will Jennings, you may have heard some of his later collaborations, such as Tears In Heaven (Eric Clapton) and My Heart Will Go On (Celine Dion).

This content and all Song Meaning articles were created and written by Top 40 Contributing Editor Ed Osborne. © 2024 Ed Osborne. All Rights Reserved. In addition to these song meaning articles, Ed has written our “Year in Music 1960s-1990s” articles.

Produced by:

  • Steve Winwood
  • Tom Lord-Alge

Lyrics Written by:

  • Steve Winwood
  • Will Jennings
  • Holland-Dozier-Holland


  • “Roll with It” was nominated for two Grammy Awards in 1989
    • Record of the Year
    • Best Male Pop Vocal performance