No Elliott Smith on this one. He will get his own list some day. Otherwise half the spots would’ve been his songs.
I also excluded all songs that are mainly about heartbreak. They are their own thing and also deserve a list.

1. Soko – Sweet Sound of Ignorance (2017)
2. Aimee Mann – Save Me (1999)
3. Badly Drawn Boy – A Minor Incidence (2002)
4. Cat Stevens – Trouble (1970)
5. The Smiths – Asleep (1987)
6. Alexander feat. RZA – Truth (2010)
7. Eels – Not Ready Yet (1996)
8. Mac Miller – Good News (2020)
9. Jon Brion – Song for Caden (2008)
10. Daniel Johnston – Like A Monkey In A Zoo (1980)

Honorable Mentions:

Jeffrey Lewis – Anxiety Attack (2005)
Jon Brion – Little Person (2008)
Soko – How are you (2012)
Kimya Dawson – Walk like Thunder (2011)
Kimya Dawson – 12/26 (2006)
Sia – Breathe Me (2004)
Joanna Sternberg – This is not who I want to be (2019)
Kendrick Lamar (feat. Beth Gibbons) – Mother I sober (2022)
Labrinth (feat. Zendaya) – I’m Tired (2022)

Eels’ album “Electro Shock Blues” (1998)
John Frusciante’s album “Curtains” (2005)
Half of Nick Drake’s and Daniel Johnston’s catalogue of music
Also a shit ton of The Smiths and Aimee Mann