Single entry too

Frank Sinatra - My Way

Non-exhaustive and just off the top of my head:

1. C'est comme ça by Paramore
2. C'est une belle journée by Myléne Farmer
3. Manatsu no Tooriame by Utada Hikaru
4. Crash by Charli XCX
5. Hounds of Love by Kate Bush
6. Send My Love to John by Rina Sawayama
7. Today the Sun's on Us by Sophie Ellis-Bextor

Not the most... uplifting set of songs, but pretty representative. Just enough hope to keep things going, though.

Also, love that I have two French titles but only one song actually in French.

EDIT: added links for the masochistic.

single entry

the ballad of whiskers jelly

Responding late but as somebody who has trouble expressing emotions through words but easily communicates through music, I've been waiting my whole life for somebody to ask this exact question.

Edit to note that a lot of these songs are Japanese, but they have subtitles. Also it's mostly Vocaloid, which can be grating to hear to people not used to that kind of music.

First up, This specific cover of "Dark Woods Circus" gets my childhood down pretty well.
Second, experience the immediate mental consequences of that childhood with "Echo."
Third, "Abstract Nonsense." ...yeah...
Fourth, "I'm Glad You're Evil Too," finally a happy one, still my favorite song.
Fifth, "Tell Me Why"
Sixth, "Out of Sight, Out of Mind,"
Seventh, and last, describing my life today, "Life Starts Now."

It's been rough so far. I still have really, really bad days, but things are looking up. I've been genuinely happy more days in a row the past month than ever happened in the rest of my life.