Madonna’s 40 Biggest Billboard Hits. Since arriving on the Hot 100 the week of Oct. 29, 1983, with "Holiday," Madonna has earned a total of 58 chart hits, including 38 top 10s.

Last week at Billboard, we spent three days counting down the 500 best pop songs to ever hit the Billboard Hot 100, in honor of the chart’s 65th anniversary.And really, that’s just the tip of ...