After enjoying plenty of success as a member of multiple bands during the first decade of his music career in the 1960s and ’70s, Steve Winwood established himself as a popular solo artist in the 1980s. In June 1988, the talented U.K. singer, songwriter and musician released his fifth solo studio effort, Roll with It, and on August 20, the record became his first album to top the Billboard 200.
Roll with It knocked Def Leppard’s Hysteria from the No. 1 spot on the chart, albeit temporarily. It spent a week atop the tally before being replaced by Tracy Chapman’s self-titled debut. Hysteria would later return to No. 1 for four more weeks.
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Roll with It’s success was propelled by the album’s soulful and upbeat title track, which was released in May 1988. it enjoyed a four-week stay at the top of the Billboard Hot 100 that began on July 30.
Winwood co-wrote “Roll with It” with his frequent songwriting partner Will Jennings. The famed Motown songwriting team of Holland-Dozier-Holland later was added to the credits by publishing-rights organization BMI because of the song’s similarity to the 1966 Junior Walker hit “(I’m a) Roadrunner.”
More About the Roll with It Album
Roll with It was a follow-up to Winwood’s hit 1986 album Back in the High Life, which peaked at No. 3 on the Billboard 200. That album featured Winwood’s first Hot 100 chart-topper, “Higher Love.”
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The Roll with It album included two other Top-20 Hot 100 singles—“Don’t You Know What the Night Can Do?” and “Holding On,” which peaked at No. 6 and No. 11, respectively. Both songs were co-written by Winwood and Jennings.
“Don’t You Know What the Night Can Do?” got a boost from being featured in a TV ad for Michelob beer. The song topped the Billboard Mainstream Rock chart, while “Holding On” was a No. 1 hit on the Billboard Adult Contemporary tally.
A fourth single was released from Roll with It, “Hearts on Fire.” Winwood wrote that tune with his former Traffic bandmate Jim Capaldi. “Hearts on Fire” reached No. 22 on Billboard’s Mainstream Rock and Adult Contemporary charts.
Roll with It has been certified double platinum for sales of more than 2 million copies in the U.S.
In 1989, Roll with was nominated for the Album of the Year honor at the Grammy Awards. In addition, the song “Roll with It” received nods in the Record of the Year and Best Pop Vocal Performance, Male categories.
Winwood Had Topped the Billboard 200 Before
While Roll with It was Winwood’s only No. 1 album on the Billboard 200 as a solo artist, he did top the chart once before. Steve was a member of the short-lived supergroup Blind Faith, whose self-titled debut album spent two weeks at No. 1 in September 1969. Blind Faith also featured Cream alums Eric Clapton and Ginger Baker, and bassist Ric Grech. After Blind Faith broke up, Grech joined the re-formed Traffic along with co-founding member Winwood.
Winwood’s 2024 Tour Plans
Winwood currently is serving as The Doobie Brothers’ opening act on that band’s current U.S. summer tour. The trek is scheduled to run through an August 30 show in West Valley City, Utah. The next stop is an August 20 concert in Burgettstown, Pennsylvania.
Tickets for Winwood’s concerts are on sale now via various outlets, including StubHub.
Roll with It Track List:
- “Roll with It”
- “Holding On”
- “The Morning Side”
- “Put on Your Dancing Shoes”
- “Don’t You Know What the Night Can Do?”
- “Hearts on Fire”
- “One More Morning”
- “Shining Song”
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