It seems different eras have different vibes to them. The 90s is generally depicted as dark and angsty, but I've always found the 00s even more dark and angsty (ESPECIALLY the mid-00s). However, the 90s are certainly darker than the wholesome and lighthearted 80s. But which is the darkest year of the 90s? And conversely, which one is actually lighthearted and glossy? Here's my ranking:

DARKEST

1. Second half of 1999
Whilst the first half of 1999 was relatively light and carefree, the second half took a turn for darkness, misanthropy, and nihilism. This era was infamous for a few trends. The teen pop trend of 1997-early 1999 was replaced with nu metal, a dark and angsty genre of music focused on all of the previously mentioned subject matters. For this reason, you got really dark movies like Fight Club and American Beauty. Bands like Slipknot and Machine Head blew up in this era, whilst Issues by Korn became their biggest album. Even kids cartoons like Courage the Cowardly Dog were extremely dark and morbid. It seemed like such a drastic change from the first half of the year as well as the late 90s in general, setting the tone for the even bleaker year of 2000.
2. 1993
The year Schindler's List became a huge hit, as well as the commercial peak of grunge with Nirvana's darkest album, In Utero, releasing this year.
3. 1992
Very similar to 1992, with grunge being popular (including the very dark album Dirt by Alice In Chains), and dark movies. Batman Returns is considered to be one of the darkest films in the franchise for example, having a bleak tone even darker than The Dark Knight trilogy. Spawn also debuted this year, at the height of the 90s Anti-Hero trend. Overall, when people think of the 90s and grunge and the dark age of Comics and how angsty it was, 1992 is probably the year they're thinking of.
4. 1996
One poster called this "a dark year", and darker than most 90s years. I personally find 1992-1993 as well as the second half of 1999 bleaker, but 1996 certainly isn't an overly happy year. This was the year the movie Hunchback of Notre Dame came out. Marilyn Manson also broke through this year. One dark piece of media he actually failed to mention is Resident Evil, which spawned the survival horror video game genre. However, it wasn't entirely dark. I'd call the tone mixed/neutral if anything. Not grimdark, but not overly lighthearted either.
5. 1991
The beginning of the dark period that would define 1992-1993 with the rise of grunge. Albums like Nirvana's Nevermind and Pearl Jam's debut Ten came out, but this is still a transitional year. You still had some pop rap and hair metal, and some lighthearted movies like Hook. However, you also had movies like the disturbing Silence of the Lambs. Even Beauty and the Beast was darker than the Disney Renaissance's previous two films (despite still being generally kid-friendly and light, there are darker elements here). Ren and Stimpy was a dark and twisted cartoon notorious for its twisted imagery, and really hit its stride in, you guessed it, the 1992-1993 time frame.
6. 1994
This year is when grunge died with Nirvana. We had some really dark albums like The Downward Spiral by Nine Inch Nails, but grunge became replaced by commercialized post-grunge and more lighthearted genres like britpop and pop rock became more popular. If you look at film, you can see the disparity. There are some dark movies that came out like The Shawshank Redemption and The Crow, but there was also lighthearted goofy flicks like Dumb and Dumber and The Flintstones. The wholesome movie Forrest Gump debuted this year.
7. 1995
Pop culture began getting more lighthearted. This is when grunge fully died and was replaced with pop rock and R&B like TLC. Most movies weren't overly colorful and light, but also not dark. Seven is the darkest movie from this year, but it didn't do as well as stuff like Toy Story (despite the OG Toy Story having some VERY dark moments for a kids film) and Batman Forever.
8. 1998
This year is very similar to 1997, but the reason this year is darker is due to the success of the gritty war film Saving Private Ryan plus the rise of nu metal (though it wasn't REALLY mainstream yet). However, there are still very bright/colorful elements like the show Powerpuff Girls.
9. 1997
We had some dark media, like the game Final Fantasy VII and the short-lived (but unsuccessful) cartoon Nightmare Ned. South Park also came out and, despite being a cartoon, is very infamous for being violent and with lots of dark humor (but still with a fun and cheery vibe to it). But overall this year is more lighthearted, maybe TOO much. Teen pop really peaked with artists like Hanson and Aaron Carter. We also had really dumb movies like Batman and Robin, which lacked any of the grit both the first and ESPECIALLY Returns had. Besides Titanic, many of the biggest films were cheesy rom-coms. A very feminine and lighthearted year IMO even with occasional dark media. Even nu metal wasn't truly gritty yet like it would become in the second half of 1999 and 2000.
10. First half of 1999
SpongeBob and Jar-Jar Binks have their origin in this part of 1999. It's so bizarre how different they are, but the first half of 1999 truly was the peak of the teen poppy and rave part of the late 90s. Very bright and colorful with the colored iMacs debuting too.
11. 1990
This year is weird. It's like post-80s culture with pretty much no 90s elements. Even if Alice In Chains debuted this year, most people preferred to listen to dumb pop rap like MC Hammer and Vanilla Ice, plus bottom-tier glam metal like Winger and Warrant. Movies this year were quite lighthearted, such as the romantic film Ghost, wholesome Christmas comedy Home Alone, cheesy rom-com Pretty Woman, and goofy comedy Kindergarten Cop, which is probably one of the lightest movies Arnold Schwarnegger ever starred in. This year just feels so weird to me. Honestly, 1990 is basically just an 80s year passing off as the 90s, and is without a doubt the most lighthearted and wholesome year of the decade, carrying that energy from the 80s.

LIGHTEST

It seems different eras have different vibes to them. The 90s is generally depicted as dark and angsty, but I've always found the 00s even more dark and angsty (ESPECIALLY the mid-00s). However, the 90s are certainly darker than the wholesome and lighthearted 80s. But which is the darkest year of the 90s? And conversely, which one is actually lighthearted and glossy? Here's my ranking:

DARKEST

1. Second half of 1999
Whilst the first half of 1999 was relatively light and carefree, the second half took a turn for darkness, misanthropy, and nihilism. This era was infamous for a few trends. The teen pop trend of 1997-early 1999 was replaced with nu metal, a dark and angsty genre of music focused on all of the previously mentioned subject matters. For this reason, you got really dark movies like Fight Club and American Beauty. Bands like Slipknot and Machine Head blew up in this era, whilst Issues by Korn became their biggest album. Even kids cartoons like Courage the Cowardly Dog were extremely dark and morbid. It seemed like such a drastic change from the first half of the year as well as the late 90s in general, setting the tone for the even bleaker year of 2000.
2. 1993
The year Schindler's List became a huge hit, as well as the commercial peak of grunge with Nirvana's darkest album, In Utero, releasing this year.
3. 1992
Very similar to 1992, with grunge being popular (including the very dark album Dirt by Alice In Chains), and dark movies. Batman Returns is considered to be one of the darkest films in the franchise for example, having a bleak tone even darker than The Dark Knight trilogy. Spawn also debuted this year, at the height of the 90s Anti-Hero trend. Overall, when people think of the 90s and grunge and the dark age of Comics and how angsty it was, 1992 is probably the year they're thinking of.
4. 1996
One poster called this "a dark year", and darker than most 90s years. I personally find 1992-1993 as well as the second half of 1999 bleaker, but 1996 certainly isn't an overly happy year. This was the year the movie Hunchback of Notre Dame came out. Marilyn Manson also broke through this year. One dark piece of media he actually failed to mention is Resident Evil, which spawned the survival horror video game genre. However, it wasn't entirely dark. I'd call the tone mixed/neutral if anything. Not grimdark, but not overly lighthearted either.
5. 1991
The beginning of the dark period that would define 1992-1993 with the rise of grunge. Albums like Nirvana's Nevermind and Pearl Jam's debut Ten came out, but this is still a transitional year. You still had some pop rap and hair metal, and some lighthearted movies like Hook. However, you also had movies like the disturbing Silence of the Lambs. Even Beauty and the Beast was darker than the Disney Renaissance's previous two films (despite still being generally kid-friendly and light, there are darker elements here). Ren and Stimpy was a dark and twisted cartoon notorious for its twisted imagery, and really hit its stride in, you guessed it, the 1992-1993 time frame.
6. 1994
This year is when grunge died with Nirvana. We had some really dark albums like The Downward Spiral by Nine Inch Nails, but grunge became replaced by commercialized post-grunge and more lighthearted genres like britpop and pop rock became more popular. If you look at film, you can see the disparity. There are some dark movies that came out like The Shawshank Redemption and The Crow, but there was also lighthearted goofy flicks like Dumb and Dumber and The Flintstones. The wholesome movie Forrest Gump debuted this year.
7. 1995
Pop culture began getting more lighthearted. This is when grunge fully died and was replaced with pop rock and R&B like TLC. Most movies weren't overly colorful and light, but also not dark. Seven is the darkest movie from this year, but it didn't do as well as stuff like Toy Story (despite the OG Toy Story having some VERY dark moments for a kids film) and Batman Forever.
8. 1998
This year is very similar to 1997, but the reason this year is darker is due to the success of the gritty war film Saving Private Ryan plus the rise of nu metal (though it wasn't REALLY mainstream yet). However, there are still very bright/colorful elements like the show Powerpuff Girls.
9. 1997
We had some dark media, like the game Final Fantasy VII and the short-lived (but unsuccessful) cartoon Nightmare Ned. South Park also came out and, despite being a cartoon, is very infamous for being violent and with lots of dark humor (but still with a fun and cheery vibe to it). But overall this year is more lighthearted, maybe TOO much. Teen pop really peaked with artists like Hanson and Aaron Carter. We also had really dumb movies like Batman and Robin, which lacked any of the grit both the first and ESPECIALLY Returns had. Besides Titanic, many of the biggest films were cheesy rom-coms. A very feminine and lighthearted year IMO even with occasional dark media. Even nu metal wasn't truly gritty yet like it would become in the second half of 1999 and 2000.
10. First half of 1999
SpongeBob and Jar-Jar Binks have their origin in this part of 1999. It's so bizarre how different they are, but the first half of 1999 truly was the peak of the teen poppy and rave part of the late 90s. Very bright and colorful with the colored iMacs debuting too.
11. 1990
This year is weird. It's like post-80s culture with pretty much no 90s elements. Even if Alice In Chains debuted this year, most people preferred to listen to dumb pop rap like MC Hammer and Vanilla Ice, plus bottom-tier glam metal like Winger and Warrant. Movies this year were quite lighthearted, such as the romantic film Ghost, wholesome Christmas comedy Home Alone, cheesy rom-com Pretty Woman, and goofy comedy Kindergarten Cop, which is probably one of the lightest movies Arnold Schwarnegger ever starred in. This year just feels so weird to me. Honestly, 1990 is basically just an 80s year passing off as the 90s, and is without a doubt the most lighthearted and wholesome year of the decade, carrying that energy from the 80s.

LIGHTEST


Not too mention 1999 had that high school shootout with those two psychopathic teens

I always reflect on 1996, the point that the future of British tennis was in the fate for that day, for in another classroom, near by and survived, at the Dunblane school was a young Andy Murray.

Hmm.

I'm going with 1996 as being pretty dark. I don't know. Everything felt strange in 1996. The atmosphere, the songs. At the same time it was exciting though.