2008, according to my iTunes

"Walcott" - Vampire Weekend (24 on the Play Count)
"Re-arrange Us" - Mates of State (20 times)
"Send a Little Love Token" - The Duke Spirit (17)
"Buildings and Mountains" - Republic Tigers (13)
"Set Me Free" - The Heavy (12)
"MC Chris is Dead" - MC Chris (12)
"Time to Pretend" - MGMT (11)
"Furr" - Blitzen Trapper (9)
"Senor and the Queen" - The Gaslight Anthem (9)
"Bye Bye Bye" - Plants and Animals (8)
"Sex on Fire" - Kings of Leon (7)
"Resistance Street" - What Made Milwaukee Famous (7)
"Boracay" - The Little Ones (6)
"Wishing Well" - The Airborne Toxic Event (5)
"Grinding Halt" - The Muslims (5)
"Tiger Mountain Pleasant Song" - Fleet Foxes (4)
"Little Bit of Feel Good" - Jamie Lidell (4)

I'll have to take iTunes's unbiased word for these. I can't believe I listened to Walcott that many times. But then looking at, say, The Gaslight Anthem song, some of these I don't even know the words to. And just seeing that Lidell song on there makes me nose hurt like I walked into a freshly bleached school bathroom.

You'll be happy to know, Poetic and Divine, that I listened to "Kind Fate" (by The Wax Standard) four times. Beat out all my Michael Franti.