Classics : The first person to win a million dollar in "Who wants to be a millionaire?"
Here is the last question being answered by him. Chooses the phone line option, and calls his dad... not to ask the question as he knew the answer pretty well ...
The rest are in this video. Year 1999. Note that there was no Youtube in 1999, and digital cameras took at best stills at VGA resolution. But this video got viral regardless.