Steve Winwood – Roll With It

First Hit #1: July 30, 1988

If we’re creating a narrative for 1988, for the most part it has been in a bit of a funk, listening to slightly dark ballads and crying in its beer. It wasn’t until now that the year managed to get over whatever wronged it and decided to cut loose. Roll With It is almost a response to a ballad-heavy first half of the year. First, it’s a trumpet laden bit of dance music, significantly more upbeat than most of the songs that came before it on the chart. Second, well, it’s actively encouraging everyone to have a bit of fun and stop being so serious. Roll With It is kind of an optimistic rallying cry, saying that no matter what happens the singer and the person he’s singing to can make it through whatever bad things are happening around them, provided they roll with it. Considering a year top-loaded with songs about seemingly unsuccessful love, it’s kind of a refreshing message. The charts are based around the popularity of singles, the whims of record executives and the vagaries at fate, so it’s always unexpected when they manage to accidentally build a narrative out of the chaos.

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One Response to Steve Winwood – Roll With It

  1. RBerman says:

    Steve Winwood’s second and final trip to the top is, like the similar “Sledgehammer” by Peter Gabriel, a slice of bouyant Otis Redding R&B homage. Winwood enjoyed quite a second chance career here for a few years, even hitting the charts with a re-release of “Valerie” from the early 80s. People just liked his clear Phil Collinsy sound.

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