I once played TOC number 1 with 3 oldster locals. When I took out my 2-iron, the eldest (who was my partner and was called "The Undertaker" by his fellow New Club members) said:
"You're not gonna insult the old lady with an iron, now, are ya?"
In poor contrast to all the great holes on this list, for me, one of the scariest tee shots in golf is at my home club: Shoreline Golf Links, #18 - during any match play scenario. OB on both sides. Wind always howling straight across from left to right. The scar-tissue from the mishaps at the home club is far more psychologically scary than anything that could happen to me at say Dornoch #1...
I've won on a number of times on that hole by laying up on the tee shot and making 5. However, the advantage to the bold player who laces one at least 240 on the fly straight gets, is pretty high.