The No. 1 Song On August 12, 1988 Sounds Even More Breezy Today

The song entrenched at the No. 1 spot on Billboard's Hot 100 on August 12, 1988, was a brand-new single from Steve Winwood, but the easygoing, infectious, and party-starting "Roll With It" sounded like it came out of the mid-20th century. Also coming out of the mid-20th century: Winwood himself. A musician who became mega-successful before he hit 21, he was a teenager with a preposterously much older-seeming and seasoned voice when he first emerged with the Spencer Davis Group in the 1960s.

After the rock star chameleon who played in an absurd number of bands had stints with the likes of Traffic and Blind Faith, he embarked on a solo career, but the big hits dried up by 1982. Abandoning the keyboard-based sound he'd developed, Winwood re-emerged in the late 1980s with throwback soulful rock, first hitting No. 1 with "Higher Love" in 1986, and then two years later with "Roll With It," a rock song from 1988 that sounds even cooler today. Here's how Winwood channeled his own passions and classic rock background to create the longest-running No. 1 single of 1988, the four-weeks at No. 1 summer smash, "Roll With It."

Will Jennings wrote the words for all six of Steve Winwood's Top 10 hits — "While You See a Chance," "Valerie," "The Finer Things," "Higher Love," "Don't You Know What the Night Can Do?" and "Roll with It," which spent most of August 1988 at No. 1. Those lyrics are about not letting hardships get in one's way, and they match up with the joyful, brassy, and sensual tune composed by Winwood. To really make it sound like 1960s soul, Winwood recruited two members of the Memphis Horns, the iconic horn section that played on countless R&B records. "I think 'Roll With It' harks back to the music I was listening to when I grew up and when I started playing music,'" he told Rolling Stone (via "The Billboard Book of Number 1 Hits"). "It's probably more like the kind of thing that I might have done with Spencer Davis."

In 1990, Winwood and Jennings faced allegations that they may have taken too much from older, copyrighted R&B music when crafting "Roll With It." Motown Records' '60s-era house songwriting team of Brian Holland, Lamont Dozier, and Edward Holland were added to the credits of "Roll With It" after a lawsuit was filed and settled, alleging strong similarities to "(I'm a) Roadrunner," a 1966 hit they composed for Junior Walker and the All-Stars.