(some links move or break from time to time)
Early before 2005:
How not to do Unit Selection TTS - Laurence Olivier ad for Coca Cola
NPR on Valentines Day 2002: the male voice is Gary Mora.
IVR "the Amtrak lady" from SNL and another at Hulu
Siri has spawned a whole new category:
a joke on Siri (Virtual Assistant) from "The Big Bang Theory" tv program
same here youtu.be/lIjuMhX_nlA
Automotive
Automotive UI Learning too much? (image)
Buick's heart attack detection from NPR's Wait Wait Dont Tell Me, October 2014
GM Lead Engineer on the Volt, and Peter Sagal, from NPR's Wait Wait Don't Tell Me, June 2016
IVR (telephone)
IoT
Interesting voices
Lowest voice in the US https://www.youtube.com/watch?v=i9P1ymFCxf0#t=23s
Vocal fry by Faith Salie
How to spoof DeepMind's ASR:
And, yes, I know my names means "stupid" in Chinese (笨), "of" in Arabic ( بن ), and "excrement" in Japanese (便). Associating a "toilet" with "convenience" is done in Chinese, Japanese, and English.
Serious stuff, still fun
realtime recognition continuous: https://speechlogger.appspot.com/en/