1983-1984
1. "Holiday" (1983)
From her self-titled debut album, "Holiday" was the first of Madonna's songs to make Billboard's Hot 100, peaking at number 16. It is now one of her signature songs.
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2. "Borderline" (1984)
Madge's second single broke the top ten on U.S. charts, which was impressive for a newcomer. In this video, look for a very young John Leguizamo, who plays a friend of Madonna's boyfriend.
3. "Like a Virgin" (1984)
This song was Madonna's first number one on Billboard's Hot 100, probably due to her legendary appearance at the first-ever MTV Video Music Awards. Rolling around in a wedding dress, Madonna sang this song and cemented a mutually beneficial relationship with music videos.