Songs I have learned (in order of when I learned them)
1: Of Angels and Angles—Decemberists
2: I Am Trying To Break Your Heart—Jeff Tweedy
3: Every Rose Has Its Thorn—Poison
4: Dude (I Totally Miss You)—Tenacious D
5: Tribute—Tenacious D
6: Kyle Took A Bullet—Tenacious D
7: Wish You Were Here—Pink Floyd
8: Radio King—Jeff Tweedy
9: Let My Love Open The Door—Pete Townsend
10: Broken—Seether
11: Like A Rock—Bob Seger
12: Ruling Class—Jeff Tweedy
13: Nutshell—Alice In Chains
14: Luna—Smashing Pumpkins
15: Via Chicago—Wilco
16: Karate—Tenacious D
17: Ingrid Bergman—Billy Bragg
18: Theologians—Jeff Tweedy
19: California Stars—Jeff Tweedy
20: Summer—Blackfield
21: Wishful Thinking—Wilco
22: Kielbasa—Tenacious D
23: Jesus Etc. —Wilco

Songs I might try to learn
The Road
Mayonaise
I Could Have Lied
Undertow
How To Fight Loneliness
Title and Registration
Some Paul Thorn songs
Some other Jeff Tweedy songs