Madonna and Letterman: A F*cking 20-Year Chronology

Twenty-one years ago on Late Night with David Letterman, Sandra Bernhard ran through her "jokes" too quickly, scrapped for material, and dragged her friend out onstage. That woman was Madonna, a noted cultural trailblazer and fellow proponent of belted jean shorts. As Letterman and the pop phenomenon exchanged barbs about her role in David Mamet's Speed the Plow, neither likely guessed that the future would hold at least seven more episodes of Madonna-Letterman badinage. Their most recent "encounter" (as Madonna put it) occurred on last night's Late Show. Let's revisit the video chronology of Madonna's most memorable moments with Dave, and we'll even spare you the times she was promoting a children's book.

1. Without You I'm Bombing

Madonna's first appearance on Letterman was both convoluted and completely staged, but not in a George McFly way. Bernhard, a scheduled guest, brought Madonna onstage to amp up rumors that the two were sexually involved, much to Letterman's chagrin. Too much squawking and onstage eye-rolling occurs, but both Madonna and Bernhard slide in a couple of winning bons mots while dressed like jazzy camp counselors who scissor.

2. Take a F*cking Bow

In what is likely the most famous Letterman interview of all time, Madonna spouted the f-word 13 times and told the former Indianapolis weatherman to smell her panties. Twenty-one minutes of grand parlor room discomfort! Madonna blithely discusses Charles Barkley's genitals and calls Letterman unfunny before, well, the audience turns on her for good. Rosie O'Donnell claimed in later years that Madonna was encouraged to swear by Letterman's producers, but she doesn't need excuses: I'm on Madonna's side here. Dave earned her sauciness when he introduced her as having "slept with some of the biggest names in the entertainment industry."

3. From G-String to Six-String

Six years passed before Madonna sat back down with Dave, but she made sure to commemorate their reunion with an ill-fitting Elvis in Hawaii jumpsuit. Thanks! Promoting her album Music and reflecting on her cigar-hacking, f-bomb-laden heyday, Madonna conducted an overly civil conversation with Letterman that culminated in her volunteering to play guitar and perform her single "Don't Tell Me," which is still her best post-Y2K single. Letterman's a little more pandering in this interview than is de rigeur, but predicting Madonna's willingness to chat is something like nailing down the artistic credibility of Shanghai Surprise. A humiliating crapshoot, indeed. Bonus: She said "shit" twice on air, which reminded us that she was still Madonna and not Carlos Leon's undead, amateur lobotomy experiment.

4. Not-So-Mean Girl

Madonna's primness can be a real problem. In 2007, her interview in support of that weird animated movie Arthur and the Invisibles was frightfully sedate and ominously offset by her newly acquired adamantium biceps. Letterman does well and brings up the pressing '07 issue of Britney and Lindsay's missing underwear, and Madonna perks up and handles the subject with aplomb. "[Once] I brought you a pair of my underpants," she says. "Maybe you can send them to Britney."

5. Cheesy Goodness, But No Pepperoni

Last night, following the release of her giant greatest hits package, Madonna reemerged on Late Night as a single mother with enigmatically taut cheeks just trying to make it in this economy. After arriving onstage on the shoulders of the New York Rangers (and bumping her head during the entrance), she cackled like a B-movie arachnid and declared she'd rather "get run over by train" than getting married again. A diplomatic conversation ensued before Dave whisked Madonna next door for her first-ever slice of New York pizzeria pie. She ate least three bites, which is the kind of out-of-character boldness you learn to relish from Madonna in 2009. And Dave? Dave ditched her there and brought out his next guest Harry Connick, Jr. Madonna totally should've called upon Sandra Bernhard. Oh well. There's always appearance #9.