Many years ago, at early DEF CONs before 2000, I became a critic of Hacker Jeopardy after some of the questions had wrong answers. The host had written the questions and answers but got some wrong. The next year I offered to sanity check them before the game and did so, finding a few errors shortly before the game started. I think this happened a year after that but my memory is fuzzy as to how many years I helped. At some point I offered to help write questions well in advance of the next DEF CON and began scribbling ideas in a notebook. I found that notebook recently!
Below were to be the proposed topics and questions in order of difficulty. I have not included a few questions which would have been acceptable to most attendees back then, but shouldn’t have been in hindsight. One of the questions revolved around ‘open secrets’ of two individuals in the scene, one being John Draper and the other continuing to be an open secret to this day.
After a recent DEF CON which had a Hacker Jeopardy that had every team miss which port Telnet is on , I wonder how teams would do with these. Some may be subjective, but they had more widely-known backstories at the time.
- This charlatan is best known for her delusions of grandeur, Erik Bloodaxe reading her mail, the FBI harassing her, and more. [Carolyn Meinel]
- PGP is a lost concept to this charlatan. [Winn Schwartau]
- This well-trained monkey/charlatan hacked a bank once. [Ira Winkler]
- This charlatan can help you learn the SECRETS of hacking a public library or BBS. [Knightmare]
- This charllatan is master of using ‘grep’ for his IDS at NASA! [Dan Ridge or ‘B-grep’ or ‘wizkid’]
Which DEF CON
This first answer on my list strikes me as wrong. My own memory today says only ~ 200 showed up to DEF CON 2, but now I wonder if it was really ~ 400, which would explain an answer of ~ 300 showing to DEF CON 1. But conventional wisdom and our poor memories often cite the first one only having ~ 100 there. Anyone have a more definitive memory?
- Only 300 people showed to this DEF CON 
- Which two hackers were thrown out of the Aladdin at which DEF CON? [Pete Shipley / Voyager @ 5]
- The Sahara was serving minors Heineken beer at which DEF CON? 
W’ere here to help…
- We are hackers who will be glad to narc you for teenpron.gif! [EHAP or Ethical Hackers Against Porn]
- We are hackers who will be glad to get you legal counsel like the other 0 we have helped. [HDF or Hackers Defense Foundation]
- Spending a quarter million to prove what everyone knew by building “DeepCrack” is the only thing we’ve done in years. [EFF]
- We’ll be glad to repost your advisories six months after you do! [CERT]
- Pay us thousands, and our 17 year veterans will babble … err teach you to hack Japanese banks. [se7en]
- What does RSA stand for? [Rivest, Shamir, Adleman]
- Win95 SSH supports what flavors of encryption? [Idea, 3DES, Blowfish]
- Name one ITAR loophole [printing or missile]
- What crypto engine is unix crypt() based on? [Enigma]
Everything under the Sun
- Sun was derived from what flavor of Unix, while Solaris hails from which? [BSD vs SysV]
- What is the default debugger installed with Solaris? [adb]
- How many returns does it take t overflow AND exploit a vulnerable binary on the sparc architecture? 
(I only had notes for 4 questions, nothing written out)
- SunOS 4.0.3
- Unicos 7.x
The idea for this was Unix commands that were also commonly joked about euphemisms for sexual activity. There were many, many more back in the day but I only ended up with three questions in my notes for some reason.
- Foreplay as ‘stinky pinky’ [finger]
- This function might lead to child processes [fork()]
- These two commands make 69 [head + tail]
Ultimately these were never used I don’t believe, and as I recall, the host and question writer for Hacker Jeopardy at the time said ‘yes’ to collaborating on questions in advance of the next convention, but did not follow-through at all so the idea died off.