Two music videos were released for this song. Fitting with the retro theme, Madonna's version has the newly platinum-blonde singer cruising in a 1957 Ford Thunderbird convertible with her friends (her real-life friends, fashion designer Erika Belle and actress Debi Mazar, are featured). James Foley, who also worked on "Live To Tell
" and "Papa Don't Preach
," returned as director.
The second video was chosen among many amateur entries for MTV's "Make My Video" contest. The winning video, directed by Angel Garcia, follows a young girl's first meeting with her perfect guy.