Lame answer, but the early-2000's. Mainly because that was when the internet and general culture peaked, imo. The 90's and 80's were kino, don't get me wrong. It's just that dial-up sucked balls, and I don't want to go back to using that shit. The early 2000's was still well within the Wild West era of the internet. With shit like Newgrounds and YTMND and less fake and gay social media sites dominating the web like it does today. The early 2000's was the beginning of meme culture, and the internet in those days was still a place you could use to escape the bullshit of real life. As opposed to nowadays, where the internet is pretty much an extention of real life. Also, you could say whatever the fuck you wanted on the internet. The internet was just less corporate and regulated back then, and it should've stayed this way. While this is more mid-late 2000's, YouTube in it's early days was undeniably way better than it is now. Back then, it was way less corporate and people weren't trying to make careers out of producing audio-visual goyslop for zoomers. YouTube didn't have to cater to advertisers nor lazy as fuck parents who plopped their toddler in front of a tablet all day to rot their developing brains on Elsagate shit. People just made videos for fun, and it was the purest form of online video content. Shit was pretty sweet.
Plus, gaming in the early 2000's kicked ass. The Gamecube for instance was the quintessential Nintendo console, imo. Very few retarded gimmicks like the Wii and later consoles, while also still differentiating itself from it's PS2/Original Xbox competition. Main flaws with the Gamecube was lack of online play and use of proprietary mini-discs instead of normal DVD's like the PS2 and Xbox. If the Gamecube had those two features, it would've sweeped the floor with the PS2 and Xbox. Some of the best Nintendo games came from the Gamecube era. Including Super Mario Sunshine, Smash Bros Melee, Metroid Prime, Wind Waker, etc. Even a few good 3rd-party games, such as Resident Evil 4. Not to say the PS2 and Xbox were shit. They were also good systems. The Xbox especially, imo. Being the first console that wasn't from a failing company to support online gaming. I never got to experience the Xbox much while it was still in it's heyday, but from what I've heard, playing the original Halo and shit like Counter-Strike online kicked ass for the console playerbase at the time. The 6th generation was a time where online gaming was starting to get good, while also not being monetized to hell in the forms of shit like DLC and online subscriptions and microtransactions, etc.
PC gaming also started getting good around the 2000's. With the release of Half-Life 2 and the beginning of indie games in the form of Cave Story. Both released in 2004, alongside Nintendo's best portable system the DS. A system which had a big library of awesome games, plus the ability to play older GBA games. The stylus gimmick was also way less intrusive than the later Wii's motion control bullshit. The DS did this while also being fairly powerful for a 2004 handheld. Being able to render decent-looking 3D models and being one of the first major handhelds to support online gaming.
People overall back then were just less political, for the most part. While you still had virtue-signalling patriotism spergs in the early 2000's, you could mostly ignore them. Unlike the wokeoids of the 2010's and today. People back then could just get along with one another. Even if they had opposing political views. Political correctness was less of a thing, back then. You could actually make offensive jokes without having some leftist faggot scream down your throat over it. You didn't have to walk as much on eggshells constantly
What I'm trying to say is the iPhone and the Obama administration was the beginning of the end for the golden age of Western culture.