3. David Letterman Interview, 1994
Madonna’s appearance on The Late Show on March 31, 1994, made for the most censored television broadcast in network history. The star came under fire for her coarse language—the word “f**k” alone was uttered over 13 times—as well as speaking exclusively in sexual innuendo, including a memorable moment in which Madonna is asked if her noise ring hurt when it was put in, leaving her with no choice but to clarify that “it always hurts when it’s put in.” Yikes, what would Carson do?