Never played any of them, but I did buy all the Crash games (and all the Spyro games) on PSN since they are half off now.
You're in for a treat.
Crash 1 is ridiculously frustrating with its save system, to the point that I feel that I'll probably just use the password to unlock everything to get all the levels at this point, so I can play through them all at my own pace.
Crash 2 is my favourite game of all time, I'm incredibly bias but there's really little I can fault it for.
Crash 3 has some great platforming levels, but half the game is spent not playing as Crash doing actual platforming, which puts it down for me.
Crash Team Racing still holds up great, probably the best kart racer until Sonic & All Stars Racing Transformed, but I still probably prefer CTR due to nostalgia.
They're all jam packed with secrets and whatnot that are tricky to find in a lot of places; some being downright obscure, but you'll get so much more satisfaction completing them without using walkthroughs.
The Spyro games are great too if you've never played them. I've not played much of them myself though; finished the first area on the first, played the demo of 3, and read about the second in the Official PlayStation magazine years ago and have longed to play it ever since.
Try the GBA ones out, they're actually closer to Naughty Dog's games in atmosphere than Wrath of Cortex was imo.
Yeah, I've heard really good things about those actually. I'll definitely consider trying them sometime.
Edit: Does anyone have any solid tips on how to hit the shortcut on Cortex Castle on CTR? It's been eluding me for ages how to get it consistently, and it's the only track I have left on time trial. I've been using PAL Penta for the time trials.