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Right! One of the famous initial iPhone OS exploits involved a vulnerability in LibTiff. Decoding a crafted .tiff in Safari would grant the site's javascript root access.

It was actually a clever "Slide to Jailbreak" rather than a click.

https://en.wikipedia.org/wiki/JailbreakMe

You're correct. jailbreak.me I think it was called

It was always amusing to visit the Apple store and see a jailbroken iPhone on display when this vulnerability worked.

And it was resurrected later on - by comex, I think.

Yep, it was a pdf parsing exploit I believe.