My music is...complicated

I literally have over a thousand songs saved on my flashdrive (all of which I manually selected one at a time over the years). I listen to music a lot while playing online chess and usually I change songs between games based on my mood and especially based on the game results, situations and my mental state at the time. 

Today it has a typical rated session (rating went down slightly, but overall didn't move too much). I thought it would be funny to share some of the songs I heard, in order, (although this isn't all of them I listened to today). 

They might seem pretty "random" but to me most of these songs have references I understand or I heard from memes or something like that xD

Any questions to my "randomness" today? xD

bernie sanders

What about it? xD 

The video memes kind of says it all. Oh, I also showed this song to @Marcyful and got it stuck in their head lol

The first song is very random indeed! xD

I say yes to Yes!

That song was intended to cheer everyone up (especially the children) after Japan had a tsunami and earthquake disaster in 2011. It is nice to spread a little joy to people - especially when it hardly costs anything to spread. Kindness is free to give

well ok the first two seen a bit sus but yeah flying dutchman seems cool and interesting

Not "sus" but okay, the second video I wanted to post the shorter version of the song I originally heard; this is the official full version if you were interested:

Over a thousand  songs on your flash drive? You have the songs backed up in case the flash drive fails, right?

Yeah, thanks for the concern. I have those songs (and everything else) backed up on several flashdrives and also some SD cards. 

There have been probably half a dozen times I've been saved by losing data, or cut how much data I lost and had to manually get back.

I guess most people just use Spotify or YouTube videos, but I like the method I've got. It comes with a ton of work, but it also has its benefits too

Hey, I knew one song, and one seemed slightly familiar.

Do you have Rick Astley never gonna give you up on there?

Interesting although my music taste leans more toward “suspense and drums” 

#16 You know the rules, and so do I.

I challenge anyone to post 11 YouTube music videos that are MORE random than OP 😀

Of course