Vogue

Warner Bros. wanted a new song for the B-side of Keep It Together, and Craig Kostich approached Shep Pettibone. Pettibone recorded the basic music on a budget of 5,000 dollars. Madonna flew to New York two weeks later, wrote most of the lyric on the plane, and recorded the vocals in single takes in a booth converted from a closet in a basement studio on West 56th Street. Pettibone suggested a rap naming classic film stars. She had seen dancers voguing at The Sound Factory The executives decided it was too good for a B-side, and it became the lead single from I'm Breathless, the Dick Tracy soundtrack album, on 20 March 1990.

It is a house song with disco influences, in A flat minor at 116 beats per minute, and the first verse does not begin until a minute and a half in. It topped the Hot 100 for three weeks and the UK chart for four, reached number one in more than 30 countries and has sold more than six million copies worldwide. AllMusic's Erlewine called it Madonna's finest single moment.

David Fincher directed the video on 10 and 11 February 1990 in 16 hours at Burbank Studios. Its imagery drew on the painter Tamara de Lempicka and Hollywood photographers including Horst P. Horst, and the dancers Luis Camacho and Jose Gutierez of the House of Xtravaganza auditioned for her at the Tracks nightclub in New York. It earned nine nominations at the 1990 MTV Video Music Awards and won Best Direction, Best Editing and Best Cinematography. In 2012 VMG Salsoul sued over a 0.23-second horn sample from Love Break, and a judge found for Madonna and Pettibone, a decision the Ninth Circuit affirmed.

Live

At the 1990 MTV Video Music Awards she performed it with a Marie Antoinette theme, and Rolling Stone ranked the performance sixth in the show's history. She also performed it at the Super Bowl XLVI halftime show in 2012 and on the Celebration Tour. Beyoncé's The Queens Remix of Break My Soul in 2022 interpolates it.