David Letterman's wackiest guest appearances

David Letterman's wackiest guest appearances: Madonna spent most of her surly interview smoking a cigar, swearing and creating awkward double entrendes for Dave.

(CBS)

2 of 6

Madonna in 1994

Madonna spent most of her surly interview smoking a cigar, swearing and creating awkward double entrendes for Dave.

Copyright © 2009, The Chicago Tribune