David Letterman’s Most Hilariously Obscene Interview

The year was 1994, and Madonna had some things she wanted to share.
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The year was 1994, and Madonna had some things she wanted to share.
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In the weeks leading up to David Letterman’s last night hosting the Late Show, favorite guests like Bill Murray, Julia Roberts and Adam Sandler have stopped by to congratulate Dave on his 33 years of service and wish him well. On the whole, it’s been a very entertaining, nostalgia-tinged lovefest: Roberts got a smooch, Murray jumped out of a cake, and Sandler sang a song both funny and intensely sweet.

That’s well and good, but Letterman was always the one figure on television who was ruthlessly unsentimental, pleasantly prickly, and reliably skeptical of the whole show-biz affair. As such, we want to remember one of Dave’s weirdest, most uncomfortable, and seemingly interminable interviews: when the wise-cracking man from Ball State encountered the sexually-voracious, potty-mouthed pop star from Michigan.

David Letterman’s last night hosting the Late Show, favorite guests like Bill Murray, Julia Roberts and Adam Sandler have stopped by to congratulate Dave on his 33 years of service and wish him well. On the whole, it’s been a very entertaining, nostalgia-tinged lovefest: Roberts got a smooch, Murray jumped out of a cake, and Sandler sang a song both funny and intensely sweet.

That’s well and good, but Letterman was always the one figure on television who was ruthlessly unsentimental, pleasantly prickly, and reliably skeptical of the whole show-biz affair. As such, we want to remember one of Dave’s weirdest, most uncomfortable, and seemingly interminable interviews: when the wise-cracking man from Ball State encountered the sexually-voracious, potty-mouthed pop star from Michigan. 

In 1994, Madonna donned a floor-length black dress, combat boots, got really high onendo” (the buds of the world’s strongest marijuana plant), and greeted Dave with, “Incidentally, you are a sick f***.” Then, she gave him a pair of used underwear, and demanded he smell them. Then, she mused to the wall, wondering if “Funny Dave Letterman” were an oxymoron.

Lewd, combative, and clearly stoned, Madonna was the perfect storm—uninterested in any questions the host offered, yet still energized and witty enough to turn those questions into raunchy double-entendres. Did she know Charles Barkley? Yes, and the long boom mike reminded her of Chuck. Did it hurt when her nose ring was put it in? Madonna thought Dave was inquiring further about Charles Barkley, and whatever he had to “put in.” Did Madonna mind that she was periodically joked about on the show? Madge inquired, Periodically? You can’t through a show without talking about me… or thinking about me.

Throughout, Madonna fellated a cigar and used the F-word fourteen times, a talk-show record that stands to this day. In the final minute, she asked: Have you ever smoked “endo”? Dave hadn’t, and after that cautionary tale, we doubt he ever did. Watch, and marvel at David Letterman stretched to his limits: bitter, funny, and flirty, even in the face of disaster.