In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
Everyone is hot. The David Fincher-directed video for “Roll With It,” Steve Winwood’s second and final #1 hit, takes place in some sort of idealized Southern juke joint that only lets sexy people in the door. Winwood, 40 years old and still plenty hot himself, bangs on a Hammond organ and makes passionate faces at the camera. He’s got suspenders over his white shirt and sweat sprayed on his face. The people in the crowd, most of whom are a whole lot younger and Blacker than Steve Winwood, hump each other in elaborately choreographed ways. Fincher shoots everything in sepia-toned black and white. It all looks dazzling, in the same way that an exceptionally well-made beer commercial looks dazzling.
Fincher, still four years away from making his feature debut with Alien 3, knew how to make a beer commercial. The same year that he shot the “Roll With It” video, Fincher also made a transfixingly coked-out Colt 45 ad with Billy Dee Williams. By that point, Fincher had been directing music videos for years — for Rick Springfield, for the Outfield, for the Hooters, for Johnny Hates Jazz. (“Roll With It” was the first song with a David Fincher video to hit #1. It wouldn’t be the last.) For “Roll With It,” Fincher did the obvious thing. He constructed Steve Winwood the Southern fantasyland that Winwood so clearly wanted. “Roll With It” is a copy of a copy, a piece of sheer pantomime. In a late-’80s environment when beer-commercial aesthetics dominated, it was a towering smash.
By 1988, Steve Winwood had been doing pantomime for more than half his life. With the Spencer Davis Group, Winwood had been a British blues-rock child star, a guy who wowed audiences and peers by moaning and hollering in ways that sounded so much like the blues records that British Invasion types fetishized so lovingly. With Traffic and Blind Faith, Winwood stayed in the rock-establishment mix for decades. In the ’80s, Winwood made a conscious decision to play toward his mass-entertainer side, moving to New York and hiring a high-powered manager. Winwood stacked his 1986 album Back In The High Life with a dream team of star collaborators, and he finally reached #1 with the slickly bland “Higher Love,” which had both Chaka Khan and Nile Rodgers in its supporting cast.
After “Higher Love,” Winwood got to #8 with the bloopy Back In The High Life ballad “The Finer Things.” (It’s a 4.) Soon afterward, Winwood reached #9 with a remixed version of “Valerie,” a 1982 single that had only made it as high as #70 in its first run. (It’s a 5.) Suddenly, Steve Winwood was the most popular he’d ever been. The Spencer Davis Group had signed with Island Records in 1964, when Winwood was 16, and he’d been with the label ever since. But after the success of Back In The High Life, Winwood left Island and signed a $13 million deal with Virgin.
Winwood co-produced his 1988 album Roll With It with Tom Lord-Alge, the guy who’d engineered Back In The High Life and who’d remixed “Valerie.” Winwood had just married his second wife, an American woman, and he’d moved to Tennessee. Winwood had always loved Southern blues and soul, and Roll With It was his attempt to tap into those traditions. In the end, though, Roll With It really just came across as a slick ’80s version of the stuff that Winwood had made decades earlier with the Spencer Davis Group, which itself was a slick ’60s version of the blues records that Winwood loved. Roll With It sounds like an album from the kid who kept a neon Budweiser sign on his dorm-room wall because he thought that made his room look like a seedy bar.
For “Roll With It,” his album’s first single and title track, Steve Winwood worked with a few musicians with deep Southern roots, including the Nashville studio keyboardist Mike Lawler (who’d had a short run with the Allman Brothers Band in the early ’80s) and with the Memphis Horns, the legendary horn section who’d played on dozens of Stax classics. Winwood recorded “Roll With It” in Toronto, not in the South, but he was definitely trying to evoke some kind of classic American grit.
In fact, Winwood was probably trying too hard to evoke that stuff, or maybe he was just copying. Either way, various publishers noticed how much “Roll With It” sounded like “(I’m A) Road Runner,” the 1966 single from Jr. Walker & The All Stars. Holland-Dozier-Holland, the great Motown songwriting team responsible for “(I’m A) Road Runner,” got retroactive songwriting credit for “Roll With It,” and they deserved it. (“(I’m A) Road Runner” peaked at #20. Jr. Walker & The All Stars’ two highest-charting singles, 1965’s “Shotgun” and 1969’s “What Does It Take (To Win Your Love),” both peaked at #4. “Shotgun” is a 9, and “What Does It Take (To Win Your Love)” is a 7.)
In “(I’m A) Road Runner,” you can hear the song that Steve Winwood wanted to make with “Roll With It.” Winwood clearly intended for “Roll With It” to be a sweaty, funky old-school workout. But Winwood was a pop star in the ’80s, and ’80s pop stars were simply not capable of sweaty, funky old-school workouts — at least not the kind that Winwood envisioned. Winwood had made sweaty, funky old-school workouts in the ’60s, but the ’80s studio-pop environment made that impossible. “Roll With It” has its horn-stabs and organ-blurts in the right places, but there was never any mistaking the ’80s sheen on the track. The song’s pastiche comes off as forgery, and Winwood comes off like he’s trying to sell you some inferior consumer goods.
Maybe the problem is that Steve Winwood does not sing about being a road runner on “Roll With It.” That might’ve been fun. Instead, “Roll With It” is a vague song about persistence, about making it through tough times because you know that things will be better in the future. In his showy gargle-squawk, Winwood sings about how when life is too much, you can’t stop and lose your touch. Winwood co-wrote the song with his regular collaborator Will Jennings, a lyricist whose work will appear in this column again. I can’t believe Steve Winwood really needed help to write lyrics as bland and cliché-riddled as the ones on “Roll With It,” but maybe Winwood didn’t trust himself to come up with those lines about someone’s love being as good as money and as sweet as honey on his own.
“Roll With It” held the #1 spot for longer than any other single in 1988, partly because the song was a cross-format hit. “Roll With It” rolled to #1 on the Adult Contemporary and Mainstream Rock charts, and it even reached #30 on the R&B charts. (It’s the only Steve Winwood song ever to touch the R&B charts.) Steve Winwood was not the first British boomer to sell Americans a halfassed copy of American music, and he would not be the last. But in its sheer, galling, sincere obviousness, “Roll With Me” grates on me even harder than most of the songs that fit that description. As far as I can tell, Steve Winwood really thought he was pulling Otis Redding moves. He was not.
“Roll With It” looked and sounded like a beer commercial, and Winwood followed it up with an actual beer commercial. Around the same time as “Roll With It” came out, Winwood starred in a Michelob ad campaign set to his song “Don’t You Know What The Night Can Do?.” Soon afterward, that song became his next single. Winwood later insisted that Michelob had licensed the song, that he hadn’t written a Michelob jingle. But if he had written the song as a jingle, would it have sounded any different? (“Don’t You Know What The Night Can Do?” peaked at #6. It’s a 2.)
“Holding On,” another wretched Roll With It single, made it as high as #11, and the album went double platinum, but that would be the end of the weird little Steve Winwood commercial renaissance. After “Don’t You Know What The Night Can Do?,” none of Winwood’s singles cracked the top 10. Winwood’s next album, 1990’s Refugees Of The Heart, stalled out at gold, and its lead single “One And Only Man” peaked at #18. After that, Steve Winwood was no longer a pop-chart threat.
Winwood reunited Traffic in 1994, though the new lineup was just him and drummer Jim Capaldi. Winwood played almost all the instruments on Traffic’s reunion album Far From Home, and he played Woodstock ’94 with that version of the band. Since then, Winwood has come out with three solo albums, and he’s steadily played arenas and outdoor sheds ever since. Next summer, Winwood heads out on a big American tour with Steely Dan. (The tour was supposed to start tomorrow, but it only just got pushed back.) I can’t think of too many combinations less appealing than that one. You won’t catch me at any of those fucking shows. I don’t roll like that.
BONUS BEATS: “Roll With It” is one of those gigantic hit songs that no longer exists, so it hasn’t made too many cultural appearances since 1988. But I think Ani DiFranco might be referencing “Roll With It” on a 1991 song that’s also called “Roll With It.” Here’s that song: