Every disc-based generation has been pretty similar, but it's gotten better over time.
I'd say Playstation/PSX was probably the worst because it was the generation where developers were still figuring out how best to load stuff. In subsequent generations, especially by the PS3/360, even though the load times were bad, developers were adept at hiding loading sequences through gameplay moments like crawling through bricks or opening doors. People complain about these sequences now, another "Lara Croft squeezing through rocks moment" but it's much better than going to a menu screen and staring at "loading....." which could take anywhere from 20 seconds to 2 minutes, and then you wouldn't be sure if the game froze or not.
Load times on PSX games were horrible because the game frequently would load at first boot, a long loading time, and then for 3D games it would load between rooms. When you died, it'd load again, and frequently take as long as the initial load. Compare this to the PS2 which had huge, vast worlds and relatively quick loading times once the game loaded. Developers also figured out how to improve this within the generation over just a couple years. GTAIII had the very long loading time to launch the game, and then also loaded every time you went between islands. Vice City improved it a bit to prevent you from backing into a loading area by giving a small grace-location over the bridge in the center of the map that was available on both zones. By San Andreas it was pretty amazing that the entire game world could load initially and if you were going around the open world even in an airplane the world never loaded again, that was incredible.
Also any game that required you to swap a disc to load the next area is worse than anything we've had in the last 10 years. In MGS when you had to swap discs in that center area that was really rough especially if you backtracked wrong or were stuck on where to go next. Or Driver 2 for PSX, you had to insert Disc 1 to launch the game and get to the main menu, and then you'd go to load your progress and be prompted for Disc 2, you couldn't just launch the game off of Disc 2 and pick up where you left. I feel like there's a generation of gamers today who will never know how bad we had it and the shit we put up with 20 years ago, hahaha
Even recent games with notoriously long load times like Red Dead Redemption II, once the game loads, you're pretty much in the game world with minimal loading, mostly seamless transitions between gameplay and missions, pretty much instant reloads when you die. So that initial 2minute loading time is extremely long, but once you're in the game it's fairly rare to ever see another loading screen beyond a few seconds.
I never played C64 or Amiga, and didn't play much of the Philips CDI, Atari Jaguar, etc., to really comment on the loading times. Mostly thinking about the mainstream successful consoles.