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Personally, I didn't realize I've done so much.

Reconcile Our Differences (Dave Matthews)
Changes In Latitudes, Changes In Attitudes (Jimmy Buffett)
The Boxer (Simon & Garfunkel)
Sweet Baby James (James Taylor)
True Companion (Marc Cohn)
Fire & Rain (James Taylor)
American Tune (Simon & Garfunkel)
When He Cries (John Gorka)
For The Beauty of Wynona (Daniel Lanois)
Grace Is Gone (Dave Matthews Band)
Breakfast At Tiffany's (Deep Blue Something)
Drop-D Medley (Bartender > The End (Doors) > Bartender > DDTW)
Only Wanna Be With You (Hootie & The Blowfish)
Nothing Now (Original)
Wandering (James Taylor)
Losing My Religion (REM)
The Maker (Daniel Lanois)
I'll Back You Up (Dave Matthews)
You Can Call Me Al (Paul Simon)
So Damn Lucky (Dave Matthews)
I Was Just Thinking (Teitur)
Stay Or Leave (Dave Matthews)
I Can Still Make Cheyenne (George Strait)
Much Too Young (To Feel This Damn Old) (Garth Brooks)
Every Rose Has Its Thorn (Poison)
Flake (Jack Johnson)
Kathy's Song (Paul Simon)
Moonshadow (Cat Stevens)
You & Me (Lifehouse)
Sorry So Sorry (Howie Day)
Babylon (David Gray)
Boulevard Of Broken Dreams (Green Day)
Gone Country (Alan Jackson)
Oh My Sweet Carolina (with Sarah) (Ryan Adams)
Spring Way (Original)
Something In The Way She Moves (James Taylor)
Collide (Howie Day)
Three Marlenas (The Wallflowers)
Lover's Cross (Jim Croce)
Blackbird (The Beatles)
I Will Follow You Into The Dark (Death Cab For Cutie)
75 Numb (Original)