The title track “Like a Prayer”, “whose lyrics could be about carnal or religious transcendence”, was the first single to be released from the album in March 1989.[16] Jim Farber of Entertainment Weekly said, “The gospel-infused title track demonstrates that her writing and performing had been raised to heavenly new heights.”[39] The song was featured in a television advertisement for soft drink manufacturer Pepsi, although the ads were canceled following the song’s controversial music video.[40][41] In the video, Madonna incorporated many Catholic symbols such as stigmata and burning crosses, and a dream about making love to a saint.[11] Holden of The New York Times said the video “surpasses Madonna’s earlier music videos in its heady swirl of sacred and profane images.”[9] The scandal led “Like a Prayer” to the top of the Billboard Hot 100, becoming Madonna’s seventh U.S. number-one single. It also reached number one in Australia, Belgium, Canada, Ireland, Italy, Spain, and the United Kingdom, among other countries.

The album’s second single, “Express Yourself”, is “an unabashed groove tune” which is “smart and sassy.”[7] Madonna preaches female empowerment, and advises girls not to settle for less than they are worth. It peaked at number two in the U.S. and was a top five hit worldwide. The music video was inspired by the classic Fritz Lang film Metropolis (1927). Its budget of $5 million made it the most expensive music video in history at the time it was made (it is currently the third most expensive of all time).[42] It was followed by “Cherish”, an adult contemporary hit which also peaked at number two on the Hot 100. The song “manages a nod to the Association song of the same title” and “makes savvy retro-rock references.”[7] The album’s fourth single, “Oh Father”, is “an homage to Simon & Garfunkel and tells the story of an abused child.”[43] The video, inspired by Orson Welles’ Citizen Kane (1941), reunited Madonna with “Express Yourself” director David Fincher.

“Dear Jessie”, which “boasts kaleidoscopic Sgt. Pepper-isms”, was released in Australia, the United Kingdom, and some other European countries.[7] “Keep It Together” is inspired by Sly and the Family Stone.[14] It was the sixth and final single to be taken from the album. In Australia, it was released as an double A-side with “Vogue”, resulting in a number one hit.