I liked this first single from her debut eponymous album (released today in 1983) best, even though "Lucky Star" was drilled the desire for fingerless lace gloves into my brain during babysitting stints. And, in what I just realized is branding, ca. 1983, she's wearing the same outfit in the "Lucky Star" video, just with fingerless lace gloves?
"Holiday" wins, and not just because the aerobics-sans-highcut-leotard video is performed in front of a live Dutch Masters painting.
It's really one of her best songs, one of the few from that debut that she didn't write herself. Plus, that piano riff at the end -- is this the last non-synth instrument played on a Madonna track until "Don't Tell Me?"
I love remembering first hearing this song, thinking she was another Shannon or the like, and realizing, no--now, this is someone completely different than anyone else at the time. She's not British, she's not black. She's (going to be) timeless. And the song, too. To wit: