Because I know each of you is on the edge of your seat waiting to see my votes, I won't make you wait any longer. As an added bonus, I've also added degree of difficulty in my decision (1-10, 1 being easy as pie; 10 being next to impossible).
My college years:
Ignition (1)
Fell in Love with a Girl (2)
Last Nite (10) (I had to listen to both about three times each and I ended up deciding that I love the verses and chorus in 99 problems, but I'm not positive they work together quite as well as they could)
In Da Club (8) (I like Wilco. A lot. But what song sounds more like that period to me? In Da Club.)
Crazy in Love (2)
Hey Ya (10) (Two of the best songs in this bracket and they go head to head in round 1? Hey Ya likely should win the whole thing though.)
Cry Me River (3) (The best song JT has made.)
Hot in Herre (2) (Much like with the Wilco comment...this song just screams mid-college to me.)
When we were still good at sports:
Since U Been Gone (1) (I unabashedly love this song. Arcade Fire is fine, but I wouldn't have picked Rebellion.)
Mr. Brightside (1)
Take Me Out (2) (Really, they pick Jesus Walks as their Kanye song?)
My Love (5) (Don't love either song)
Umbrella (8) (See previous comment and amplify it. Can we bring in a pinch hitter? Where the hell is Crazy by Gnarls Barkley?)
All My Friends (9) (A really, really tough decision. I think the older I get, the more I love LCD Soundsystem, but Yeah is a classic mid-2000s track.)
Rehab (2)
Drop It Like It's Hot (1)
More good songs than you realize years:
Rolling in the Deep (5) (The Robyn song is also really, really good.)
Party in the U.S.A (10) (Perhaps the catchiest song of the millennium against a song I adore. Miley's pop tune is just too good though. I can't get it out of my head even after listening to 20 other songs since then.)
Bad Romance (1)
Teenage Dream (10) (Much like PITUSA vs. Kids. Teenage Dream, to me, is just about the perfect pop song about teenage love. It really gets everything right. Had they picked Listzomania, I'm not sure what I would have done.)
The House That Build Me (1) (Ke$ha should never be allowed to record music again.)
Single Ladies (7) (I don't like Single Ladies at all, but I loathe that Vampire Weekend song. Put anything else up against Single Ladies and my vote would shift.)
Empire State of Mind (1)
My Girls (1) (It won't win this matchup, but it should.)
Bzzzzzzzzzzzzzz:
The House That Heaven Built (3) (I never really felt the Ni**as in Paris vibe.)
Red Solo Cup (1) (Don't like Red Solo Cup, very much dislike A$AP's track.)
Springsteen (1) (Fantastic song.)
Pyramids (3)
Blurred Lines (3) (Meh for both, but Blurred Lines will stick around longer.)
Midnight City (8) (The first tough matchup in this bracket. Never underestimate the vengeance of Taylor Swift, but M83's song is better.)
Get Lucky (1)
Call Me Maybe (1) (I don't hate all electronica, just most. Skrillex is no exception.)