80's Guilt #04: Madonna "Dress You Up" (1985)

In the imaginary alternate bizarro-universe where Madonna somehow faded into obscurity or retired from music after the True Blue LP, she is considered the greatest 80's female pop singer. But in our universe, she got increasingly irritating between 1989 and 1996, leaving behind a bad taste in our mouths. While her efforts to keep things interesting were appreciated, her 90's songs simply weren't as good as they were in the beginning, even though everyone pretended they were just as good or better. (Britney Spears is currently receiving suspiciously similar treatment, an artist who coincidentally also peaked within her first three LP's.)

In 1999, a year after after Madonna released Ray Of Light and entered a (predictably calculated) phase where she showed "maturity," MTV started airing GAP commercials where models creepily stared into a camera and sang in unison to songs such as Depeche Mode's "Just Can't Get Enough," Donovan's "Mellow Yellow," and "Dress You Up", a single which was popular during the 80's but somehow lost popularity after not being chosen to appear on 1991's The Immaculate Collection.

The GAP commercial (coincidentally well-synched with the launch of Napster) was the first time many people had heard "Dress You Up" in nearly a decade, shedding new light on her early forgotten singles "Burnin' Up" and "Angel" while also pumping some freshness into previously stale singles such as "Lucky Star," "Borderline" and her early movie-soundtrack-ballads "Crazy For You" and "Live To Tell." We'll post a few of these here...