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Recently I had a weird experience while listening to this song.

It sort of gives a weird feeling of melancholy, but a cheerful vibe at the same time. It's weird. The most curious part is that it's from a freaking Wario game out of all things.

My theory is that it might have to do with me playing the game when I was younger and the longing of the simpler times back then. The song always stuck out with me.

What do you think? Are there any songs that make you feel similar?

the BF1 soundtrack has a lot of tracks like you described, but i think the ending theme for all of the Russian centered maps fit what you look for the most

Discovered this song while I was going through a confusing time in my life. A lot of good moments and bad ones, this song helped me get through them. It was only recently that I realised that this song is just Biggie talking about how he fucked another man's girl and almost getting cought. But regardless, this song will always remind me of those times when I was sad and how it made me happy.

Another Biggie song that makes me feel happy and sad at the same time would be this remix of Juicy. When I first discovered it I was in a hip hop / rap phase and this was one of the songs I found. Since I didn't know who Biggie was at the time, the lyrics, voice, and instrumentals gave me a vibe that this was an underground rapper from NYC reminiscing on how he went from rags to riches and I felt happy for him. I would later find out that this rapper I never heard of before is this guy named The Notorious B.I.G. aka Biggie Smalls and he was murdered some time after the original song was made, and it made me feel sad becouse this remix made it sound like Biggie had a great life, which I'm sure he did before he died. This remix also introduced me to Biggie and Emancipator.

In case you couldn't tell yet, I really like Biggie's music.

Kinda the same reason that you had OP.
This was my very first Sonic game(s) (well, besides from "Ultimate Flash Sonic"), this song in particular has that sweet nostalgic feeling with it.
You kinda miss the old times when you were a kid, you know, the world was bright, simple, you rarely knew what "negative feelings" were, you were happy most of the time (sometimes you still are, just not as much), there were your very early childhood friends that you lost contact with nowadays, you never really complained about anything in life, etc.
But, at the same time, those old memories are also your happy memories, you feel happy for remembering some of the best moments of your life through this song, you know, moments like learning to ride the bike for the first time and saying "MOM! DAD! I DID IT!", or just playing with your childhood friends with something simple like hide-n-seek, volleyball or even video games.
This song is just simply beautiful, and I love it… thanks Sonic.

There are many Silent Hill tracks (not just from the original game but from all over the series) that are packed with balanced blends of those kind of feelings. I think this one serves as a good example.

It's a happy song, but it gives me this feeling of nostalgia. Like memories the carefree times I'll never get back.

Well, as long as I'm posting music today,

(Also a fantastic video here.)

Post-rock generates a powerful ebb and flow of emotions. This single song by Mogwai leaves an immense electrifying chill throughout. The first three seconds tell you everything to come, and still leaves you in wonderment and surprise by the end.

Leaves an impression of a sense of scale, and what can truly be accomplished with music.

Don't Stop Me Now by Queen. The songs a fucking banger but its the end that gets me every time because the end of the song reminds me of Freddy Mercury's death. The end comes abruptly and seemingly too soon and with his vocals at the end always brings to my mind Freddy ascending to a better place.

It's just so serene that it makes me sad that my life will never reach this level of comf

Get a feeling so complicated etc.

Bump

My favorite track from the OST.
Has this comforting vibe that gives me a feeling of nostalgia, makes me yearn for the days of being a 6-year old kid again.