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.
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.