Here are some songs that I find myself playing here and there:
Weezer - Mykel and Carli
The Shins - So Says I
Billy Bragg - Jailcell Blues (from Memaid Avenue)
Silver Jews - Random Rules
Silver Jews - The Wild Kindness (and a few others by them)
Radiohead - Lucky
Hank Williams - Lovesick Blues
Willie Nelson - Redheaded Stranger
Johnny Cash - I guess things happen that way
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Here are some harder ones that are fun, but I've added them for completion:
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Pixies - Caribou
Radiohead - Street Spirit
Beatles - Blackbird
Modest Mouse - Styrofoam boots/it's all nice on ice
And what got me good at fingerstyle guitar was my brief obsession with Elliott Smith's music. Like, I've memorized how to play about 10 of them. (Primarily Say Yes, Waltz #2, and Angeles...)
Okay, I think that just about does it. I've given away my entire internal mental state of my twenties.