A lot happened for Madonna between the years between her 1984 smash album Like a Virgin and its 1986 follow-up, True Blue. The singer appeared in her first two movies: The young-love drama Vision Quest— for which she recorded “Crazy for You”, her second No. 1 single—and the smartly fizzy comedy Desperately Seeking Susan, which produced an all-time classic with “Into the Groove”. As if that wasn’t enough, she delivered her third chart-topper, the ballad “Live to Tell”, for her then-husband Sean Penn’s bleak crime film At Close Range. “Live to Tell”, which would become the first single off True Blue, was the first in a string of era-defining hits that Madonna would co-write and co-produce with Patrick Leonard. You can hear the singer maturing as both a lyricist and a vocalist on “Live to Tell”—but it’s hardly the only moment of artistic growth to be found on True Blue. The second single, “Papa Don’t Preach”—yet another No. 1 hit—found the Material Girl tackling social issues for the first time. And “Open Your Heart”, fittingly, finds Madonna at her most open-hearted, with one of her most vulnerable vocals. It’s also one of several True Blue tracks in which Madonna goes deeper into the 1960s girl-group groove, along with “Where’s the Party”, “Jimmy Jimmy” and, of course, the title track. Elsewhere on the album, “White Heat”—one of a handful of tracks featuring her Like a Virgin collaborator Stephen Bray—feels like a precursor to Madonna’s role as Breathless Mahoney in the 1990 film Dick Tracy. Meanwhile, the Latin-flavoured “La Isla Bonita” inspired everything from her 1987 song “Who’s That Girl” to Lady Gaga’s “Alejandro”.