Madonna's Less-Than-Holy Appearance (March 31st, 1994)
"She's sold over 80 million albums, starred in countless films, and slept with some of the biggest names in the entertainment industry," joked Letterman before his guest sat down; apparently, Madonna felt the need to one-up Dave in the shock department after such an auspicious introduction. After ribbing the host about his "obsession" with her sex life, the pop star then proceeds to smoke a cigar and say the F-word a record 14 times. Controversy and FCC handwringing ensued, as did high ratings for Dave's show (now at CBS). It was neither the first time she'd sat across from Letterman's desk nor the last, but it's still the most memorable of her apperances.