When In Square Circle was released in September 1985, it had been five years since Stevie Wonder’s last studio album, and the delay had left critics, fans, and industry friends musing about the singer’s future. During that time, the musical landscape changed dramatically: There was the pop ascendance of Wonder’s fellow Motown alum Michael Jackson, and the rise of Prince to superstar status—phenomena that would have been impossible if not for Wonder’s trailblazing success in the 1970s. At the same time, hip-hop was making its way out of the New York boroughs and onto the charts, which were increasingly being dictated by the upstart cable network MTV. Wonder had been keeping busy during those years, in part by celebrating his own past: The singer participated in the Motown label’s epochal 25th anniversary broadcast celebration, tacked four new songs onto the 1982 best-of Original Musiquarium, Vol. 1, and was inducted into the Songwriters’ Hall of Fame. And the singer had made the occasional cameos at the top of the pop charts, duetting with Paul McCartney on the 1982 hit “Ebony and Ivory,” and releasing a global smash with the Oscar-winning “I Just Called to Say I Love You," from the soundtrack to The Woman in Red (the tune would displace Prince’s “Let’s Go Crazy” from the No. 1 spot on the Billboard charts). The first single from Circle sits squarely in the middle of Wonder’s legacy, while also fitting into the current pop-R&B moment. Two years earlier, the Motown-heavy soundtrack to the boomer drama The Big Chill had revived interest in the label’s peak period, and “Part-Time Lover”—with its undeniable synth bassline, effervescent chorus, and scatted refrain (assisted by Luther Vandross)—was a bona fide Reagan-era reimagination of Motown’s famed Sound of Young America style. No one is going to call In Square Circle Wonder’s best album—it’s merely the last one that could be called “very good”—and apart from some interesting electronic experimentation (“Never in Your Sun”), the misses here outnumber the hits. But after nearly a quarter-century in the music industry, the 35-year-old Wonder had one classic left in him: The sumptuous ballad “Overjoyed,” which ranks among the best 1980s slow jams, and which fit in perfectly with the quiet storm radio format personified by Vandross. Wonder would stay musically active after In Square Circle, but it was his last gasp as an artist directly dialoguing with his moment—fittingly, at a moment when popular culture started hyper-referencing its own past, one that Wonder himself had helped shape.