The overclock I really remember was my Celeron 500, run at 75 FSB, it was already outdated when I got it but it saw a lot of gaming (CS, Max Payne, Q3 etc. and older games), divx movies which were still quite a novelty back in 2001. The vid cards were S3 Virge PCI 4MB and Voodoo2 SLI but despite their old age I was tremendously CPU limited.
This poor rig died because of running on FSB 83, which looked fine if you pretended to ignore some random instabilities. It also had a weird bug : I had dropped it and after that, it could only boot if run outside the case.
My single worst purchase was done for this rig, I thought the PCI bus had too much stuff crammed it and sharing the bandwith (one 2D vid card, three 2D vid cards, sound card, NIC) so I bought a used SiS 6326 AGP, which had a fine 2D picture but was slow as hell.. I could watch the GUI elements be drawn and video playback was unusable. Mindboggling. I had to get the S3 Virge back in, and realized how great S3 Virges were, these cards did deserve their reputation for 3D gaming but were cheap and high performing 2D cards
Much later, my other overclock : the Sempron LE-1100, a single core 65nm K8 at 1900 MHz, which got an easy 25% overclock (with undervolting). Without o/c, it trounced my older XP 2400+ already (with which I had killed the motherboard again). The stock heatsink was more than adequate, dead silent. This CPU did put very little heat out, I later learned they used it underclocked on netbooks and called it Athlon Neo.
It was awesome.
Also, I lost all overclocking ability on this mobo (which is still my PC's mobo) when I tried a pair of bad ram sticks to try them out. sigh.. two memory slots were fried and it didn't ever boot again with o/c, even with bus at 201MHz instead of 200. Which makes me wonder why it boots at all at 200 and is 100% stable still.