Like the suggestions here, and think we're getting close to a final format. I'll restate after every revision. Hopefully, we'll have this hammered out before Thursday so we can read, review, suggest any final tweaks. Here's a modification of what I posted, incorporating Derek and Marc's suggestions on the point-scoring, which is good and ensures that, even in the scenario that Derek outlines, where Stu comes up badly against him in every round, Herr Watson at least garners at least one vote (presuming he can bring himself to vote for himself).

With regards to randomly ending up with the same opponent repeatedly, that tend to happen. So we either need to decide to allow randomness to a point, then intervene with a rule like, 'can't face the same opponent more than 3 times', though not sure how you resolve that once it happens and other matchups are already decided.

An alternative: since we happen to have arrived at 10 rounds total and we have a total of 5 possible matchups per person, maybe we say we each have to face an opponent twice. Open to either scenario. Just no complaining if you don't like your repeat matchup.

I'll print out and bring some tear sheets that we can use, with each person's name and round listed, in order to help keep track of the voting (and ensure that someone just doesn't repeatedly toss their own name in multiple times per round). Each person will then get 10 sheets of six names, with the round listed by the name, that they can then tear off and place in the hat, bowl, pot, dutchie, etc. Should expedite the process and cut down on penmanship errors.

Revised Rules

1) Names of each player are written on pieces of paper and placed in a hat. Matchups are randomly selected by draw and order of spins then occurs in the order of the draw. For an example, let's assume the names are chosen as follows: Mike, Derek, Brian, Kyle, Marc, Stuart. Mike then plays a song from one of his decades, followed by Derek. Assuming we stick with the random assignment.
2) We vote on which of the two songs just played that we like better; votes are tossed into the hat, and we move on to the next two songs. Votes are entered but not tallied until the end of the 5th round; Derek's suggestion of waiting until 5th round. I like this but suspect some will want to know how they are doing before getting halfway through the tourney. Perhaps we count after 3 rounds instead? Provides enough suspense while also ensuring people have time to adjust if they feel that their songs are 'cutting it' with the group.
3) We move onto the next matchup, Brian v. Kyle, then Marc v. Stu.
4) A giant board records point totals after they are tallied
5) We move onto the next round of pairings, either randomly assigned or actually assigned.

Suggestions for additional rules:

-Year requirement: Suggested modification: Player has the option of whatever year to play in the matchup, but cannot play the same year three times consecutively.

-Song Length: You may exceed the 5 minute length no more than twice in the contest. All songs will be cut off after 8 minutes. Players have the option of fast forwarding in order to highlight a section of the long song if they wish. Assume everyone is okay with this one.

-Tie-breaker at the end of the rounds: If two or more players are tied in points at the end of 10 rounds, a sudden death final round occurs where each surviving player plays one song (chosen by a random selection) and we vote on the best played. The tied players do not get a vote in this round (that way, if an odd number are tied, we have a chance of quickly determining a winner).
Assume we're okay with this one as well.