Most iconic artists have the one album that cemented their status, breaking sales records and establishing their chokehold on the culture.

Michael Jackson had Thriller. U2 had The Joshua Tree. Prince had Purple Rain.

Madonna, arguably, had two such albums. Two years after Like a Virgin became a global smash and the top-selling album by a woman, she dropped True Blue in 1986 and managed to top herself.

This collection fell just short of Like a Virgin‘s U.S. sales, but was a worldwide phenomenon, reaching #1 in a record 28 countries and selling more than 25 million copies globally. It cemented her status alongside Michael Jackson as the biggest star of the 80s.

Madonna co-wrote every song on True Blue and co-produced the album with longtime collaborators Stephen Bray and Patrick Leonard. The record label that hesitated to give her the creative reins on her previous album knew better by now.

On True Blue, she sought a more mature sound, introducing strings, acoustic guitars and non-programmed drums to her usual mix of dance-heavy tracks. She tackled teenage pregnancy on unlikely hit ‘Papa Don’t Preach’ and embraced Latin influences on ‘La Isla Bonita.’

In ‘Open Your Heart,’ Madonna explored romantic longing and produced a video that had quite a corrupting influence on my 14-year-old self.

This is mostly a bright and joyous album, and likely the sweetest thing ever inspired by a romance with Sean Penn.

Amid the bubblegum pop is ‘Live To Tell,’ the greatest ballad Madonna ever recorded. Written for Penn’s film At Close Range, this moody masterpiece was the first of three True Blue tracks to reach #1 on the singles chart (two others peaked in the top five).