Originally on The Daily Show when Craig Kilborn hosted, and now on The Late Late Show also hosted by Kilborn, this bit came at the end of every interview. Some cheesy music starts up, often cutting off a rambling anecdote, and Craig exclaims "It's time for 5 Questions!" to the wild cheers of the audience. For full effect, the intro clip to 5 Questions is taken from The Story of Ricky.
The first question is always about geography. From there, the questions could be anything from opinions (to Mike Myers: "Canada: What went wrong?") to forcing guests to say stupid things (to Ben Stein: "Finish this song lyric: She's a super freak, super freak...") to just about anything else. Kathy Ireland was the first person to get only 1 out of 5 correct, a feat duplicated by Carrot Top and Ben Stein, although to be fair, Ben was given extremely hard questions in payback for a special Daily Show-themed episode of Win Ben Stein's Money. Nobody has scored 0 out of 5. Bill Murray was the first to get 5 out of 5. Many other guests, most notably John Tesh, have also aced the quiz. However, you can't beat Bill, you can only tie him.