Songwriting and guitar playing extraordinaire Conor Oberst has spent the better part of the last two decades playing deeply captivating songs that have rightfully gleaned comparisons to the great Bob Dylan. As part of his project with Mike Mogis and Nathaniel Walcott, Bright Eyes, Oberst has released gut-wrenching gem after gem, fully investing himself in the emotional capabilities of music that conveys a bold desire to understand life. Oberst brazenly ventures into the most emotionally damaging territories, pushing at questions of love and life, no matter where it takes him. 

His often heartbreaking catalog has the power to transport us to a very specific time and place, from the depths of our most nostalgic memories. Oberst's quivering vocal or angst-driven cracks instantly lodge themselves under our skin. Here are twenty of the biggest Bright Eyes songs that have deeply moved us and soundtracked our most intimate moments. Special thanks to Katie Skau for creating the artwork for this playlist.

20. "A Song To Pass The Time"

19. "Lua"

18. "Four Winds"

17. "Light Pollution"

16. "Shell Games"

15. "At The Bottom of Everything"

14. "An Attempt To Tip The Scales"

13. "Arc Of Time (Time Code)"

12. "Land Locked Blues"

11. "From A Balance Beam"

10. "I Believe In Symmetry"

9. "Hit The Switch"

8. "We Are Nowhere And It's Now"

7. "Cleanse Song"

6. "Lover I Don't Have To Love"

5. "Take It Easy (Love Nothing)"

4. "Nothing Gets Crossed Out"

3. "First Day of My Life"

2. "Bowl Of Oranges"

1. "Poison Oak"