The Meaning Behind “Roll with It” by Steve Winwood and Why 3 Legendary Motown Songwriters Are Listed in the Credits

Perhaps because he doesn’t exude the same kind of flash or attitude as some of his fellow rock stars, Steve Winwood doesn’t get the kind of acclaim he deserves. Few have been as successful for as long a time in the business as Winwood, as evidenced by the fact that he scored a No.1 single at age 40 in 1988 with “Roll with It.”

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What is “Roll with It” about? Why are there some famous Motown songwriters listed in the credits? And how did the song mix with Winwood’s attitude as an artist? All the answers to come, as we look back at this exuberant hit.

Winwood Winning

Steve Winwood’s career is a marvel of resiliency and adaptability. He began as a teenager belting out hits for the soul-rock outfit The Spencer Davis Group. From there, he moved seamlessly into prog rock (Traffic) and supergroup (Blind Faith) territory, Then it was on to a solo career, which soared at the end of the ’70s thanks to sophisticated pop hits like “While You See a Chance.”

After a brief lull in the early part of the ’80s, Winwood found his footing again in a big way with the 1986 album Back in the High Life. The album paired him up with several major guest stars (James Taylor, Joe Walsh, Chaka Khan, among many others). Lead single “Higher Love” gave Winwood his first ever No. 1.

Many veteran rock artists delivered albums like that in the late ’80s that brought them back from the hard times they suffered when MTV hit the scene a few years earlier. But not all of them had the chops to back those comeback records with more success. Winwood managed that feat on the strength of a second chart-topping single that represented another artistic twist.

On a Roll

In a Rolling Stone interview from 1988, around the time of the release of the Roll with It album, Winwood explained that he didn’t shrink away from his new status as a hitmaker, but rather embraced it:

“I had a choice to go a couple of ways. If I was to say, ‘Well, I’m a musician, I’m not an entertainer,’ then I have no business going onstage with lights and trying to look … I should be in the back doing the music, and somebody else should be out front.”

That attitude played into the making of “Roll with It” in his decision to work with The Memphis Horns. The song brought him back in a way to The Spencer Davis Group days with its soulfulness.

In fact, “Roll With It,” penned by Winwood and his longtime lyricist Will Jennings, might have woken up those echoes too well. Legendary Motown songwriters Brian and Eddie Holland and Lamont Dozier were added to the credits when it was decided that the song too closely recalled the 1966 Junior Walker song “(I’m a) Road Runner.”

What is “Roll with It” About?

With Winwood’s voice (as acrobatic as ever) and those lush horns leading the way, “Roll with It” beams with positivity. Its message is a simple one that’s spelled out clearly by the title. There will be times when life throws rocks in your road. But if you stay on the path and keep your spirits high, you’ll be gliding along again in no time. Luck’ll come and then slip away, Winwood testifies. You gotta move, bring it back to stay.

Elsewhere, Winwood plays the lover man role to the hilt, as he dives into some saucy blues idioms: The way that you love is good as money / I swear by stars above, as sweet as honey. He keeps providing alternatives for the person he’s addressing for when things get tough on her: When this world turns its back on you / Hang in and do that sweet thing you do.

Winwood promises there will come a day rife with music and dancing when the hard times will be but a memory. It’s just a step up to paradise, he sings. “Roll with It” stepped up as well, giving this fantastic artist pride of place on the pop charts among much younger artists, and burgeoning his legacy as one of rock’s most reliable crowd-pleasers.

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Photo by Jerod Harris/Getty Images

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