Released in February 1984, "Borderline" became Madonna's first top 10 pop single. It remains one of the top favorites among fans and critics of her singles. The song was written and composed by Reggie Lucas who was the primary producer of Madonna's self-titled debut album. A remix by Madonna's boyfriend at the time John "Jellybean" Benitez added to "Borderline's" popularity in dance clubs. MTV's heavy rotation of the accompanying video is given credit for helping the song climb the pop charts.
"Lucky Star" followed closely after the top 10 success of "Borderline." It was released in August 1984 and debuted in the top half of the Billboard Hot 100. "Lucky Star" became Madonna's first top 5 hit single in a string of 16 consecutive top 5 releases. The accompanying video caused a stir by showing Madonna writhing on the floor and showing off her belly button.
"Like a Virgin" is the title single from Madonna's second solo album. It was the first single from the collection and appeared in October 1984 just two months after "Lucky Star." Nile Rodgers of the disco group Chic was the producer. "Like a Virgin" became a signature song of sorts for Madonna as it topped the pop singles chart, becoming her first #1 hit, and spent six weeks there. It was at the top of the chart by the end of the year, and Madonna made history of sorts when she performed "Like a Virgin" in a wedding gown perched atop a wedding cake at the 1984 MTV Video Music Awards. The accompanying music video set a high standard with much of it shot on location in Venice, Italy.
"Material Girl" was released in January 1985 just as "Like a Virgin" was vacating the upper reaches of the pop singles chart. It is another Nile Rodgers production co-written by disco star Peter Brown. The music video for "Material Girl" was celebrated for its wry tribute to Marilyn Monroe in mannerisms and style. The song peaked at #2 on the pop singles chart becoming Madonna's third consecutive top 5 hit.
"Angel" was released as the third single from Madonna's Like a Virgin album. There was no music video accompanying its release just a month after "Crazy For You," but that did not stop it from continuing Madonna's hot streak and landing at #5. Today it has been overshadowed by its 12-inch single companion "Into the Groove." The pair combined to be one of the bestselling 12-inch singles of all time. "Into the Groove" remains one of Madonna's most popular songs never released as an official single. It was included on the soundtrack to the film Desperately Seeking Susan.
"Dress You Up" became the fourth single to hit the top 5 from the album Like a Virgin. With the song, Madonna ran afoul of Tipper Gore's Parents Music Resource Center (PMRC) who cited the song for sexual content of its lyrics particularly the line, "Gonna dress you up in my love." A live video of Madonna performing "Dress You Up" in concert was used to promote the single.
"Live to Tell" was released in March 1986 and included on the soundtrack for Sean Penn's, at the time Madonna's husband, film At Close Range. It was co-produced and co-written by frequent collaborator Patrick Leonard. Eight weeks after its first appearance on the Billboard Hot 100 "Live to Tell" became Madonna's third #1 hit single. She has said that the song is about the lying that went on in her relationship with her parents. Live performances of the song created considerable controversy on the 2006 Confessions tour when Madonna performed the song while appearing to hang from a lighted cross.
While many assume that the song "Papa Don't Preach" was written directly from Madonna's personal experience or point of view, the song was actually brought to her by songwriter Brian Elliott. He says the song was written based on gossip he overheard from teen girls. Madonna only contributed minor edits in the song's lyrics. "Papa Don't Preach" reached #1 on the pop singles chart, but it also brought more controversy. A number of groups, including anti-abortion activists, accused Madonna of promoting teen pregnancy through the song.
"True Blue" is the title song from Madonna's third studio album. It was co-written and co-produced by Stephen Bray and presented a more light and distinctly retro feel after her recent controversial singles. The song was released in September 1986 and debuted inside the top 40 of the Billboard Hot 100 at #40.