When “Roll With It,” the title track of Steve Winwood’s fifth solo album, came out of the gate in the summer of 1988 and hit No.1 almost immediately, it was proof positive that that U.S. listeners were craving music that hearkened back to ‘60s rhythm and blues — they just hadn’t realized it until they’d heard it.

The song was absolutely a throwback to that life-affirming, sweaty, horn- and organ-spiked soul — like Junior Walker (“Shotgun”), Sam & Dave (“Hold On, I’m Comin’”), or maybe even that British export the Spencer Davis Group (“Gimme Some Lovin’”).

Fittingly enough, the same singer who powered Spencer Davis Group’s hits when he was a mere lad of 15, was in the pilot’s seat for “Roll With It,” 25 years later.

Winwood had been on the charts and on listeners’ stereos for just about all that time, whether creating a mind-expanding psychedelic stew with Traffic, playing stadium-filling blues with two-thirds of Cream in Blind Faith or venturing out on his own for an eclectic body of work, from the de rigueur debut in 1977, to the one-man-band introspection of Arc of a Diver in 1980, to the guest-heavy hits on Back in the High Life in 1986.

Those hits and the ones that spawned from Roll With It had come as a result of an epiphany Winwood had had about his role in popular music. Arc of a Diver had been a hit, but its follow-up, 1982’s Talking Back to the Night, had been a commercial disappointment. “I had a choice to go a couple of ways,” he told Rolling Stone in 1988. “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."

Listen to Steve Winwood's 'Roll With It'

"So you have the choice,” he continued. “You have to decide which way to go. I thought about it long and seriously, and I thought that if I sing songs to people, you can't deny it, you're an entertainer. It's not just 'I'm entertaining them' but 'I am actually an entertainer.’”

Armed with that realization, Winwood brought in producers, engineers, session musicians and guest stars (like James Taylor, Chaka Khan and Joe Walsh) for Back in the High Life, which went to No. 3 on the Billboard 200 albums chart and yielded four singles, including the No. 1 hit “Higher Love.” Winwood eschewed the famous guests on Roll With It, but otherwise followed his “entertainer” template and produced an album that hit No. 1, his only solo record to do so.

Shortly after “Roll With It” began climbing the Billboard Hot 100 singles chart, a snippet of new Winwood song, the keyboard-heavy “Don’t You Know What the Night Can Do,” began appearing in Michelob beer commercials, leading some to wonder whether Winwood had made the song to order for the beer brand, compromising his artistry for corporate dollars.

Listen to Steve Winwood's 'Don't You Know What the Night Can Do?'

Winwood was cagey about which came first, the beer deal or the song, but he was unapologetic about the partnership. “I wrote a seven-minute song,” he told Rolling Stone. “It had the word night in it, but so have other songs I've done. [Michelob] knew that. There's no way that their involvement made me present a lower-quality product. There's no way.”

It came back to Winwood’s contention of being an entertainer, not just a musician. “The fact that [the song is] on TV and in commercials — music is entertainment,” he noted. “That's the way I see it: music is entertainment, and commercials can be entertaining. So I'm happy with it.”

Roll With It also contained the gospel-influenced elegy “One More Morning,” a hymn of gratitude that is also one of his finest ballads. “Just to have this day and life starting all over, for all it may bring,” he sings. “A blessing on everything and one more song I can sing.” By the time the horns float up into the mix by the song’s end, the listener is likewise grateful for Winwood and lyricist Will Jennings’ hopeful outlook.

“Holding On” and “Put on Your Dancing Shoes” also mine the soul sound of the “Roll With It” single; the latter was an early highlight in the shows Winwood played on his summer tour in support of Roll With It. Those shows were outstanding mixes of old Winwood and new, with High Life and Roll With It songs standing proudly alongside long runs through Traffic’s “Low Spark of High-Heeled Boys” and each evening’s final encore, his old Spencer Davis Group hit “Gimme Some Lovin’.”

The shows were, above all else, entertaining. And Winwood was (and still is) an entertainer.



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