Paris Hilton and David Letterman by John Paul Filo/CBS Paris Hilton and David Letterman by John Paul Filo/CBS

David Letterman on Friday's Late Show forced the prison issue with Paris Hilton, ultimately making the heirhead feel "sad" that she paid a visit. At first owning up that her jail stint was "very traumatic," an increasingly uneasy Hilton later sought to dismiss the line of questioning by saying, "I don't really want to talk about it anymore." (To which Dave, god bless him, responded, "This is where you and I are different - this is all I want to talk about.")

"There's other stuff to talk about, Dave," Paris countered, perhaps feeling that her thoughts on the mortgage industry's collapse were going unappreciated. "Now you're making me sad.... You're hurting my feelings." Find the full video here.