Worst Songs Ever: Steve Winwood’s ‘Roll With It’

Like a good single, a terrible one reveals itself with airplay and forbearance. I don’t want to hate songs; to do so would shake ever-sensitive follicles, and styling gel is expensive. I promise my readers that my list will when possible avoid obvious selections.

Steve Winwood — “Roll With It”
PEAK CHART POSITION: #1 in August 1988

When white musicians in the late eighties thought about the black music they adored in their youth, they imagined themselves in those smokey clubs where those black musicians played for often shit money; but in those fictional clubs the white musicians were the stars, dressed like they were going to the Kennedy Center Honors, and if the black musicians were on site they served the white stars. These reveries took the form of black and white videos. Glenn Frey enjoyed his last hit with “True Love” around the time Steve Winwood released Roll With It and its succession of ever more boring and useless singles. “Roll With It” perfected and, in a sense, ended this string of boomer moves.

Winwood’s second #1, “Roll With It” was even bigger than his comeback “Higher Love” exactly two years earlier; it marked the peak of Winwood’s ridiculous High Eighties commercial watermark. The Michelob promo “Don’t You Know What the Night Can Do” followed it into the top ten, and other than a couple of top twenties remembered by VH-1 die-hards and in which Steve showed white people how to sell Quaker Oats to a non-existent black audience, dat was dat (the “Holding On” video is particularly gruesome, a Hollywood idea of what Bryan Ferry called smokey nightclub situations in his own Hollywood fantasia “2 HB”).

Since “While You See a Chance,” a surprise top five smash in 1981, Winwood has depended on his synthesizer work; with “Roll With It” he returned to piano and Hammond B3, on which he had earned the Ray Charles analogies during the Spencer Davis Group days. At the end of the Reagan era, it took some gall to remind audiences that “when times are too rough” they have to swallow their shit and accept things as they were; in the last electoral landslides of my lifetime, this served as prequel to “Don’t Worry Be Happy.” There’s nothing else to “Roll With It” except a chorus with a two-note organ interjection after Winwood sings the title hook in his prodigious I’m-choking-on-Brie timbre. Up to that moment 1988 had boasted some strange hits, from Billy Ocean’s galumphing Stones appropriation and George Michael’s anguished gay “Maggie May” to Terence Trent D’Arby’s updating of Motown tropes. George Harrison’s #1 “Got My Mind Set On You” is closest to what Winwood was after, but at least Harrison covered an obscurity that meshed with the Dirty Dancing ethos, which was to jam on MIDI technology while a few feet away Otis Redding reminded you of the eternal rock verities. Winwood wrote his own Rock Verity, or, rather VH-1 Verity, and he couldn’t even get away with it, as Holland-Dozier-Holland reminded him. It’s for this audience for whom “Roll With It” was intended.

A confused young fellow reading Wuthering Heights about to start high school, I had no idea what “Roll With It” was doing on the chart in the fucking summer. Miami’s Y-100 played it side by side with Stevie B’s “Spring Love (Come Back to Me),” Al B. Sure!’s “Nite and Day,” The Cover Girls’ “Inside Outside,” Dino’s “Summergirls,” and Fat Boys’ “The Twist.” Demographic awareness? I mean, my late thirtysomething mom blasted top forty in the car with my sister and me; were “Roll With It” and Eric Carmen’s “Make Me Lose Control” the sops? I answered my own question, I suspect.