Okay, this thread sounds like fun. It reminds me of the "Shuffle Test Tag" K-pop youtubers used to do a few years ago and it was roughly the same concept, except the song titles were supposed to be the answers of a specific list of questions (regardless of how weirdly accurate or off they were).
I don't have Spotify and whatnot, so I'll use my good ol' Ipod instead if you don't mind.

I've got about 1960 songs on it, which isn't a lot, but it suffices as far as I'm concerned.
1.
Raiven - "Zažarim" 
[MENTION=11532]EscGeek[/MENTION]
2.
Madonna - "S.E.X." 
(aka lavieenro
sexqueenbitch

)
3.
Kylie Minogue - "Speakerphone"
4.
Henry Purcell - "Fairest Isle" 
5.
Natasha St-Pier - "On Ne Fait Que Passer"
6.
Diana Krall - "Let It Rain"
7.


Salvatore Adamo & Loane - "Amour Perdu"
8.
Roch Voisine - "Je Te Serai Fidèle"
9.
Izabo - "Time"
10.
Alyosha - "Sweet People"
I didn't know what to expect, but this selection is quite representative of what I listen to actually: Eurovision entries, fun pop songs, jazz music, classical music, French chanson... Two of my six all-time favourite artists even made an appearance (Krall and Voisine). I probably would have added a K-pop song and an atmospheric electro-pop one to complete the picture.
