I'm not a huge basketball fan. It's not really my sport. I'm a baseball/football kinda guy. I know nothing of college basketball, I don't follow it. If the teams didn't have the rankings by their names, I wouldn't know who was good and who was bad. So up until 2011, I had never once filled out a bracket. But two of my co-workers were huge into college basketball, and were trying to get an office pool going, so I said I'd join, just to have a bit of fun.

Again, I know nothing of the sport, or how to pick one out. But I'm a huge music nerd, and I had a 20,000+ track iTunes library (which has since considerably grown to almost 50,000 tracks). So I came up with this method of picking my bracket. It takes about 2 hours to complete, is a bit involved, and is far too much work to go into something I ultimately care little about, but the process is fun.

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In the main iTunes library, make sure you have shuffle turned on, then hit play. The first 64 songs that play are assigned to the teams in the March Madness bracket. I just go right down the line, starting in the upper left hand corner. Right on down the left side, then up to the upper right hand corner and on down the right side. Fair is fair, keeping it random. I tend to skip over stand up comedy, duplicate artists, and I'll only use one version of a song. So if The Eagles' "Take It Easy" plays, it disqualifies Travis Tritt's.

As you are assigning songs, move the songs in that top-down order into a playlist. I usually call it "20XX March Madness". I then go to the playlist, hit shuffle on the playlist so they're good & mixed up, and that's when I start filling in the bracket.

The first song that plays in a match up is the winner and advances to the next round. 
For example: 
K-State & Kentucky are paired up (hypothetically). 
K-State gets Purple Rain by Prince, Kentucky gets Tangled Up in Blue by Bob Dylan. 
If Purple Rain plays first, I delete Tangled Up in Blue from the playlist, K-State advances.

Once a round is set. I hit shuffle, which resets the playlist back to the original order, then shuffle again, which re-shuffles the playlist into a different order, now with just the winners from the previous round. You just need to make sure that if you put songs in the playlist in order of ABCDEF, the first round goes FCBDEA, and the 2nd round goes DAEFBC (for example). Repeat the process till you have your winner.

This will be an incredibly sloppy bracket. It won't make any sense. You probably shouldn't do this if you're doing it for money. If it's just for fun, then yeah, go for it. That said... This method picked Louisville in 2013 and Duke last year. So 2 out of 5 winners is a terrible average, but pretty decent considering the methodology, and the fact that I know nothing about college basketball.

This year, here's how the Final Four looked:

#2 Villanova - "Ready for Love" by Mott the Hoople
#14 Green Bay - "All Eyes on Me" by Goo Goo Dolls
#13 Stony Brook - "In the Sun" by Joseph Arthur 
#13 Iona - "Jessica" by Juicy Lucy

Villanova met Stony Brook in the Championship, and emerged victorious. So it may be a terrible bracket, but at least I walked away with a highly ranked team... The playlist was favoring the "TBD" matches for a while, so I was getting nervous.

That's my prediction. Villanova to win it.