Compilation of clips where Late Show where Dave interviews guests with tough questions.
Hilary Duff, Paris Hilton, Lindsay Lohan, Nicole Richie, Martha Stewart.
How do you like being in jail?
Have your friends treated you differently since you've been out of the slammer?
Did you make any friends while you were in jail?
Somebody you met in prison?
Aren't you supposed to be in rehab now?
How many times have you been in rehab?
Do you drink too much?
I'm the one who's having the blackouts.
Who's taking you to rehab.
I'm three times your age and I've never been in prison.
Do you ever hear from any of the cons?
David Letterman - Asking Tough Questions - Savage